Cyanoacetamide MCR (III): Three-component Gewald reactions revisited

Journal of Combinatorial Chemistry

Volumn 12, Issue 1, 2010, Pages 111-118

  Wang, Kan ^a   Kim, Dabin ^a   Dömling, Alexander ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-CYANOACETAMIDE; BENZODIAZEPINE DERIVATIVE; CLOZAPINE; CYANOACETAMIDE; NITRILE; OLANZAPINE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY;

BENZODIAZEPINES; CLOZAPINE; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; NITRILES; SOLVENTS;

EID: 74049108885     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9001586     Document Type: Article

References (57)

1. Gewald, K.; Schinke, E.; Bottcher, H. Chem. Ber. 1966, 99, 94-100.
2. Mayer, R.; Gewald, K. Ansew. Chem, Int., Ed. Engl. 1967, 6, 294-306.
3. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. .J. Heterocyclic Chem. 1999, 36, 333-345.
4. Huang, Y., Dömling, A. Mol. Diversity 2009, in. press.
5. (a) Asinger, F.Angew. Chem. 1956, 68,413-413
6. (b) Asinger, F.; Thiel, M.; Pallas, E. Liebigs Ann. Chem. 1957, 602, 3749.
7. (c) Asinger, F.; Offermanns, H. Angew. Chem- 1967, 79, 953-956.
8. (d) Asinger, F.; Leuchtenberg, W.; Offermanns, H. Chem. Zeitung 1974, 98, 610-615.
9. (e) Asinger, F.; Gluzek, K. H. Monats. Chem. 1983,114, 47-63.
10. (a) Willgerodt, C.Ber. Dtsch. Chem. Ges. 1887, 20, 2467-2469.
11. (b) Willgerodt, C. Merck, F. H. J. Prakt. Chem. 1909, 80, 192-195.
12. (c) Kindler, K. Liebigs Ann. Chem, 1923, 431 (193), 222-224.
13. Wiklund, P.; Bergman, J. Curr. Org. Synth. 2006, 3, 379-402.
14. Meltzer, H. Y.; Fibiger, H. C. Neurovsvchovharmacoloev 1996, 14, 83-85.
15. Barnes, D. M.; Haight, A. R.; Hameury, T.; McLaughlin, M. A.; Mei, J. Z.; Tedrow, J. S.; Toma, J. D. R. Tetrahedron 2006,62, 11311-11319.
16. Mkrtchyan, A. P.; Noravyan, A. S.; Petrosyan, V. M. Chem. Heterocvcl. Comnd. 2002, 38, 238-241.
17. Zavarzin, I. V.; Smirnova, N. G.; Chemoburova, E. I.; Yarovenko, V. N.; Krayushkin, M. M. Russ, Chem. Bull. 2004, 53, 1257-1260.
18. Doss, S. H.; Mohareb, R. M.; Elmegeed, G. A.; Luoca, N. A. Pharmazie 2003,58, 607-613.
19. Roman, G.; Andrei, M. Glasnikna Hemkaritei Tehnolozitena Makedonija 2001.20,131-136.
20. Frohlich, J.; Shaifullah Chowdhury, A. Z. M.; Hametner, C. ARKIVOC 2001, 163-172.
21. Elkholy, Y. M. Phosphorus. Sulfur Silicon Relat. Elem. 2002, 177, 115-122.
22. See for example: Baraldi, P. G.; Zaid, A. N.; Lampronti, I.; Fruttarolo, F.; Pavani, M. G.; Tabrizi, M. A.; Shryock, J. C. Leung, E.; Romagnoli, R. Bioorg., Med., Chem, Lett. 2000, 10, 1953-1957.
23. (a) Bogolubsky, A. V.; Ryabukhin, S. V.; Plaskon, A. S.; Stetsenko, S. V.; Volochnyuk, D. M.; Tolmachev, A. A. J. Come, Chem. 2008, 10, 858-862.
24. (b) Hazra, K.; Saravanan, J.; Mohan, S.Asian J., Chem. 2007,19, 3541-3544.
25. (c) Hesse, S.; Perspicace, E.; Kirsch, G. Tetrahedron Lett. 2007, 48, 5261-5264.
26. (d) Kovalenko, S. M.; Vlasov, S. V.; Chemykh, V. P. Hetereatom Chem. 2007, 18, 341-346.
27. (e) Kovalenko, S. N.; Vlasov, S. V.; Chemykh, V. P. Zhurnal Organichnoi ta Farmatsevtichnoi Khimii 2006,4,43-46.
28. (f) Nikolakopoulos, G.; Figler, H.; Linden, J.; Scammells, P. J, Bjoorg. Med, Chem. 2006,14, 2358-2365.
29. (g) Huang, W.; Li, J.; Tang, J.; Liu, H. Shen, J.; Jiang, H. Synth. Commun. 2005, 35, 1351-1357.
30. (h) Treu, M.; Karner, T.; Kousek, R.; Berger, H.; Mayer, M.; McConnell, D. B.; Stadler, A. J., Comb. Chem. 2008,10, 863-868.
31. (a) Patra, B. R.; Mohan, S.; Saravanan, J. Man J. Chem. 2007, 19, 4368-4372.
32. (b) Al-Mousawi, S. M.; Abdelhamid, I. A.; Moustafa, M. S. ARKIVOC 2007, 213-221.
33. (c) Arhin, F.; Belanger, O.; Ciblat, S.; Dehbi, M.; Delorme, D.; Dietrich, E.; Dixit, D.; Lafontaine, Y.; Lehoux, D.; Liu, J.; McKay, G. A.; Moeck, G.; Reddy, R.; Rose, Y.; Srikumar, R.; Tanaka, K. S. E.; Williams, D. M.; Gros, P.; Pelletier, J.; Pan-, T. R., Jr.; Far, A. R. Bioorg, Med. Chem. 2006,14, 5812-5832.
34. (d) Weber, K. H.; Daniel, H. Liehies Ann. Chem. 1979, 328-333
35. (a) Hantzsch, A. Chem. Ber. 1881, 14, 1637-1638.
36. (b) Biginelli, P. Chem. Ber 1891, 24, 1317-1319, and 2962-2965.
37. Dömling, A. Chem Rev. 2006, 126, 17-89.
38. Wang, K.; Nguyen, K.; Huang, Y.; Dömling, A. J. Comb. Chem. 2009, 11, 920-927.
39. For example, for the 3-CR synthesis of 2-amino-l H-pyrrole3-carboxamide, see: Wang, K.; Dömling, A. Chem. Biol. Drug Des. 2009, submitted for publication.
40. (a) See ref 18d;
41. (b) Nagaoka, H.; Hara, H.; Mase, T. Heterocycles 1990, 31, 1241-1244;
42. (c) Walser, A.; Flynn, T.; Mason, C.; Crowley, H.; Maresca, C.; Yaremko, B.; O'Donnell, M. J. Med. Chem. 1991, 34, 1209-1221.
43. The Gewald-Ugi-Deprotection-Cyclization (GUDC) strategy for preparing thiophenediazepine, see: (a) HuangY. J.; Dömling, A. unpublished result;
44. (b) Walser, A.; Flynn, T.; Mason, C .J. Heterocycl. Chem, 1991, 28, 1121-1125.
45. (c) Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cara, C. L.; Cruz-Lopez, O.; Iaconinoto, M. A.; Preti, D.; Shryock, J. C.; Moorman, A. R.; Vincenzi, F.; Varani, K.; Andrea Borea, P. J. Med Chem. 2008. 51, 5875-5879.
46. (a) Mohareb, R. M.; Ho, J. Z.; Alfarouk, F. O. J., Chin, Chem. Soc. 2007, 54,1053-1066.
47. (b) Kim, M.-H.; Park, C-H.; Chun, K.-W.; Oh, B.-K.; Joe, B.-Y.; Choi, J.-H.; Kwon, H.-M.; Huh, S.-C.; Won, R.; Kim, K. H.; Kim, S.-M. PCT Int. Appl., 2007, WO 2007102679, Chem. Abstr. 147, 365516.
48. (a) Brouillette, Y.; Sujol, G.; Martinez, J.; Lisowski, V. Synthesis 2009, 389-394.
49. (b) Pinkerton, A. B.; Lee, T. T.; Hoffman, T. Z.; Wang, Y.; Kahraman, M.; Cook, T. G.; Severance, D.; Gahman, T. C.; Noble, S. A.; Shiau, A. K.; Davis, R. L. Bioore. Med. Chem. Lett. 2007, 17, 3562-3569.
50. (c) Nikolakopoulos, G.; Figler, H.; Linden, J.; Scammells, P. J Bioorg, Med., Chem. 2006, 14, 2358-2365.
51. (a) Orner, B. P.; Ernst, J. T.; Hamilton, A. D. J., Am., Chem. Soc. 2001, 123, 5382-5383.
52. (b) Antuch, W.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Sakamuri, S.; Beck, B.; Schauer-Vukasinovic, V.; Agarwal, S.; Hess, S.; Dömling, A. Bioorg, Med, Chem. Lett. 2006,16, 1740-1743.
53. (c) Haridas, V. Eur. J. Org. Chem. 2009, 30, 5112-5128.
54. Gerber, P. R.; Muller, K. J., Comput, Aided Mol, Des. 1995, 9, 251-268.
55. (a) Castanedo, G. M.; Sutherlin, D. P. Tetrahedron Lett. 2001, 42, 7181-7184.
56. (b) Hoener, A. P. F.; Henkel, B.; Gauvin, J. C. Synlett 2003, 63-66.
57. (c) Zhang, H. Q.; Yang, G. C.; Chen, J. N.; Chen, Z. X. Synthesis 2004, 3055-3059.