Sequential cyclizations of 2-isothiocyanatobenzonitrile and 2-iso cyanatobenzonitrile with α-aminoketones

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 5965-5967

  Langer, Peter ^a   Bodtke, Anja ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ISOCYANATOBENZONITRILE; 2 ISOTHIOCYANATOBENZONITRILE; AMINOKETONE; BENZONITRILE; IMIDAZO[1,2 C]QUINAZOLINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; HYDROLYSIS; STEREOCHEMISTRY;

EID: 0038305322     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01489-8     Document Type: Article

References (27)

1. For reviews of domino and sequential reactions, see: (a) Tietze, L. F.; Beifuss, U., Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze, L. F., Chem. Rev. 1996, 96, 115.
2. For reviews of domino and sequential reactions, see: (a) Tietze, L. F.; Beifuss, U., Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze, L. F., Chem. Rev. 1996, 96, 115.
3. For reviews of domino and sequential reactions, see: (a) Tietze, L. F.; Beifuss, U., Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze, L. F., Chem. Rev. 1996, 96, 115.
4. For reviews of work from our laboratory, see: (a) Langer, P. Chem. Eur. J. 2001, 7, 3858; (b) Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221; (c) Langer, P. Synthesis 2002, 441.
5. For reviews of work from our laboratory, see: (a) Langer, P. Chem. Eur. J. 2001, 7, 3858; (b) Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221; (c) Langer, P. Synthesis 2002, 441.
6. For reviews of work from our laboratory, see: (a) Langer, P. Chem. Eur. J. 2001, 7, 3858; (b) Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221; (c) Langer, P. Synthesis 2002, 441.
7. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
8. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
9. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
10. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
11. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
12. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
13. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
14. For reactions of 2-isothiocyanatobenzonitrile and 2-isocyanatobenzonitrile, see: (a) Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221; (b) Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Het. Chem. 1999, 36, 1327; (c) Besson, T.; Guillard, J.; Rees, C. W.; Therisod, M. J. Chem. Soc., Chem. Commun. 1997, 881; (d) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394; (e) Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21; (f) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854; for cyclizations of 1a and 1b with carboxylic hydrazides, see: (g) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014; see also: (h) Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.
15. Francis J.E., Cash W.D., Barbaz W.D., Bernard P.S., Lovell R.A., Mazzenga G.C., Friedmann R.C., Hyun J.L., Braunwalder A.F., Loo P.S., Bennett D.A. J. Med. Chem. 34:1991;281.
16. Cianci C., Chung T.D.Y., Menwell N., Putz H., Hagen M., Colonno R.J., Krystal M. Antiviral Chem. Chemother. 7:1996;353.
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18. Liu K.C., Hu M.K. Arch. Pharm. (Weinheim). 319:1986;188 Kottke, K.; Kuehmstedt, H.; Graefe, I.; Wehlau, H.; Knocke, D. DD 253623 (1988), Chem. Abstr. 1988, 109, 17046 Kathawala, F.; Hardtmann, G. E. Ger. Offen. 2,146,076 (1972), Chem. Abstr. 1972, 77, 48501 Kathawala, F.; Hardtmann, G. E. Ger. Offen. 2,261,095 (1971), Chem. Abstr. 1973, 79, 66385.
19. Thom A., Zinner G. Arch. Pharm. (Weinheim Ger.). 327:1994;469.
20. For related heterocycles prepared by other methods, see: (a) Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128; (b) Arnold, W.; Buettelmann, B.; Heitz, M.-P.; Wyler, R. Heterocycles 1996, 43, 2607; (c) Chern, J.-W.; Tao, P.-L.; Yen, M.-H.; Lu, G.-Y.; Shiau, C.-Y.; Lai, Y.-J.; Chien, S.-L.; Chan, C.-H. J. Med. Chem. 1993, 36, 2196; (d) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 3849; (e) Nishio, T.; Fujisawa, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2523; (f) Leistner, S.; Wagner, G.; Strohscheidt, T. Pharmazie 1980, 35, 293.
21. For related heterocycles prepared by other methods, see: (a) Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128; (b) Arnold, W.; Buettelmann, B.; Heitz, M.-P.; Wyler, R. Heterocycles 1996, 43, 2607; (c) Chern, J.-W.; Tao, P.-L.; Yen, M.-H.; Lu, G.-Y.; Shiau, C.-Y.; Lai, Y.-J.; Chien, S.-L.; Chan, C.-H. J. Med. Chem. 1993, 36, 2196; (d) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 3849; (e) Nishio, T.; Fujisawa, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2523; (f) Leistner, S.; Wagner, G.; Strohscheidt, T. Pharmazie 1980, 35, 293.
22. For related heterocycles prepared by other methods, see: (a) Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128; (b) Arnold, W.; Buettelmann, B.; Heitz, M.-P.; Wyler, R. Heterocycles 1996, 43, 2607; (c) Chern, J.-W.; Tao, P.-L.; Yen, M.-H.; Lu, G.-Y.; Shiau, C.-Y.; Lai, Y.-J.; Chien, S.-L.; Chan, C.-H. J. Med. Chem. 1993, 36, 2196; (d) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 3849; (e) Nishio, T.; Fujisawa, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2523; (f) Leistner, S.; Wagner, G.; Strohscheidt, T. Pharmazie 1980, 35, 293.
23. For related heterocycles prepared by other methods, see: (a) Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128; (b) Arnold, W.; Buettelmann, B.; Heitz, M.-P.; Wyler, R. Heterocycles 1996, 43, 2607; (c) Chern, J.-W.; Tao, P.-L.; Yen, M.-H.; Lu, G.-Y.; Shiau, C.-Y.; Lai, Y.-J.; Chien, S.-L.; Chan, C.-H. J. Med. Chem. 1993, 36, 2196; (d) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 3849; (e) Nishio, T.; Fujisawa, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2523; (f) Leistner, S.; Wagner, G.; Strohscheidt, T. Pharmazie 1980, 35, 293.
24. For related heterocycles prepared by other methods, see: (a) Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128; (b) Arnold, W.; Buettelmann, B.; Heitz, M.-P.; Wyler, R. Heterocycles 1996, 43, 2607; (c) Chern, J.-W.; Tao, P.-L.; Yen, M.-H.; Lu, G.-Y.; Shiau, C.-Y.; Lai, Y.-J.; Chien, S.-L.; Chan, C.-H. J. Med. Chem. 1993, 36, 2196; (d) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 3849; (e) Nishio, T.; Fujisawa, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2523; (f) Leistner, S.; Wagner, G.; Strohscheidt, T. Pharmazie 1980, 35, 293.
25. For related heterocycles prepared by other methods, see: (a) Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128; (b) Arnold, W.; Buettelmann, B.; Heitz, M.-P.; Wyler, R. Heterocycles 1996, 43, 2607; (c) Chern, J.-W.; Tao, P.-L.; Yen, M.-H.; Lu, G.-Y.; Shiau, C.-Y.; Lai, Y.-J.; Chien, S.-L.; Chan, C.-H. J. Med. Chem. 1993, 36, 2196; (d) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 3849; (e) Nishio, T.; Fujisawa, M.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1987, 2523; (f) Leistner, S.; Wagner, G.; Strohscheidt, T. Pharmazie 1980, 35, 293.
26. 3S (295.34): C, 65.07; H, 3.41; N, 14.23. Found: C, 65.19, H, 3.54, N, 14.14.
27. 3O (275.31): C, 74.17; H, 4.76; N, 15.26. Found: C, 74.14, H, 4.78, N, 15.14.