메뉴 건너뛰기




Volumn 5, Issue 16, 2003, Pages 2829-2832

Bartoli indole synthesis on solid supports

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; INDOLE;

EID: 0141631736     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034851y     Document Type: Article
Times cited : (47)

References (62)
  • 2
    • 84943388739 scopus 로고
    • Pyrroles and their benzoderivatives: Synthesis and applications
    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford
    • (b) Sundberg, R. J. Pyrroles and Their Benzoderivatives: Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, pp 313-376.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 313-376
    • Sundberg, R.J.1
  • 6
    • 0039835726 scopus 로고    scopus 로고
    • Teubner Studienbücher Chemie: Stuttgart
    • Breitmaier, E. Alkaloide; Teubner Studienbücher Chemie: Stuttgart, 1997; pp 116-129.
    • (1997) Alkaloide , pp. 116-129
    • Breitmaier, E.1
  • 27
    • 0033757047 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) J. Heterocycl. Chem. , vol.37 , pp. 1293-1297
    • Muchowski, J.M.1
  • 28
    • 0034686759 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6789-6790
    • Gil, G.S.1    Groth, U.M.2
  • 29
    • 0000594028 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) Org. Lett. , vol.2 , pp. 1109-1112
    • Edmondson, S.D.1    Mastracchio, A.2    Parmee, E.R.3
  • 30
    • 0034603363 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1623-1626
    • Brown, J.A.1
  • 31
    • 0034641492 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6253-6258
    • Ketcha, D.M.1    Wilson, L.J.2    Portlock, D.E.3
  • 32
    • 0002214383 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) Org. Lett. , vol.2 , pp. 89-92
    • Zhang, H.-C.1    Ye, H.2    Moretto, A.F.3    Brumfield, K.K.4    Maryanoff, B.E.5
  • 33
    • 0034647204 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5662-5663
    • Takeda, A.1    Kamijo, S.2    Yamamoto, Y.3
  • 34
    • 0034050746 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) Synthesis , pp. 429-434
    • Tokuyama, H.1    Kaburagi, Y.2    Chen, X.3    Fukuyama, T.4
  • 35
    • 0034703408 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) J. Org. Chem. , vol.65 , pp. 6213-6216
    • Rainier, J.D.1    Kennedy, A.R.2
  • 36
    • 0034607472 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) J. Org. Chem. , vol.65 , pp. 2642-2645
    • Toczko, M.A.1    Heathcock, C.H.2
  • 37
    • 0034199893 scopus 로고    scopus 로고
    • Recent examples: (a) Muchowski, J. M. J. Heterocycl. Chem. 2000, 37, 1293-1297. (b) Gil, G. S.; Groth, U. M. J. Am. Chem. Soc. 2000, 122, 6789-6790. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109-1112. (d) Brown, J. A. Tetrahedron Lett. 2000, 41, 1623-1626. (e) Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6258. (f) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92. (g) Takeda, A.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662-5663. (h) Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429-434. (i) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216. (j) Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642-2645. (k) Iyengar, R.; Schildknegt, K.; Aube, J. Org. Lett. 2000, 2, 1625-1628.
    • (2000) Org. Lett. , vol.2 , pp. 1625-1628
    • Iyengar, R.1    Schildknegt, K.2    Aube, J.3
  • 53
    • 0004127585 scopus 로고    scopus 로고
    • Nicolaou, K. C., Hanko, R. Hartwig, W., Eds.; VCH: Weinheim; Chapter 4
    • Dahmen, S.; Bräse, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R. Hartwig, W., Eds.; VCH: Weinheim, 2002; Chapter 4.
    • (2002) Handbook of Combinatorial Chemistry
    • Dahmen, S.1    Bräse, S.2
  • 54
    • 0141847218 scopus 로고    scopus 로고
    • note
    • ortho-Nitro benzoic esters failed to give indoles due to premature cleavage from the solid support.
  • 55
    • 0141847219 scopus 로고    scopus 로고
    • note
    • Merrifield resin (0.93 mmol/g) was obtained from Polymer Laboratories (UK).
  • 56
    • 0141735706 scopus 로고    scopus 로고
    • note
    • All new nonpolymeric compounds were characterized by NMR, IR, MS, and HRMS. The purity was determined using GC, GC-MS, and NMR techniques. Polymeric compounds were characterized using IR and elemental analysis (CHN) (see Supporting Information).
  • 57
    • 0141512601 scopus 로고    scopus 로고
    • note
    • Grignard reagents are commercially available from Aldrich.
  • 58
    • 0141735707 scopus 로고    scopus 로고
    • note
    • Cleavage was quantitative as judged by elemental analysis of the remaining resin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.