Solid-phase rhodium carbenoid N-H insertion reactions: The synthesis of a diverse array of indoles

Journal of Combinatorial Chemistry

Volumn 5, Issue 2, 2003, Pages 188-196

  Lee, Sang Hyeup ^a   Clapham, Bruce ^a   Koch, Guido ^b   Zimmermann, Jürg ^b   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; CARBENOID; ESTER DERIVATIVE; INDOLE DERIVATIVE; LEWIS ACID; POLYMER; RHODIUM DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; RESIN; RHODIUM;

AMIDATION; ARTICLE; PURIFICATION; SOLID; SYNTHESIS; CATALYSIS; CHEMISTRY; CYCLIZATION;

CATALYSIS; CYCLIZATION; INDICATORS AND REAGENTS; INDOLES; RESINS, SYNTHETIC; RHODIUM;

EID: 0037899991     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020079z     Document Type: Article

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27. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
28. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
29. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
30. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
31. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
32. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
33. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
34. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
35. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
36. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
37. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
38. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
39. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
40. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
41. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
42. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
43. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
44. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
45. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
46. The solid-phase indole syntheses fall into several subcategories. Fisher indole synthesis: (a) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4869. (b) Yang, L. Tetrahedron Lett. 2000, 41, 6981. (c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233. Heck: (d) Yamazaki, K.; Kondo, Y. Chem. Commun. 2002, 210. (e) Yamazaki, K.; Kondo, Y. J. Comb. Chem. 2002, 4, 191. (f) Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473. (g) Zhang, H.-C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804. (h) Yun, W.; Moham, R. Tetrahedron Lett. 1996, 37, 7189. Heteroannulation of internal alkyne: (i) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317. (j) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439. Heteroannulation of terminal alkyne: (k) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963. (l) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307. (m) Wu, T. Y. H.; Ding, S.; Gray, N. S.; Schultz, P. G. Org. Lett. 2001, 3, 3827. (n) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89. (o) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449. (p) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751. Nenitzescu indole synthesis: (q) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253. Intramolecular Wittig: (r) Hughes, I. Tetrahedron Lett. 1996, 37, 7595. Reductive cyclization: (s) Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799. Modified Madelung indole synthesis: (t) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189. Polymerbound enol ether: (u) Macleod, C.; Hartley, R. C.; Hampreacht, D. W. Org. Lett. 2002, 4, 75.
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