Dipolar cycloaddition of ethyl isocyanoacetate to 3-chloro-2-(methylthio)/ 2-(methylsulfonyl)quinoxalines: Highly regio- and chemoselective synthesis of substituted imidazo[1,5-a]quinoxaline-3-carboxylates

Journal of Organic Chemistry

Volumn 72, Issue 13, 2007, Pages 5020-5023

  Sundaram, G S M ^a   Singh, B ^a   Venkatesh, C ^a   Ila, H ^a   Junjappa, H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE SYNTHESIS;

SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

2 (METHYLSULFONYL)QUINOXALINE; 2 (METHYLSULFONYL)QUINOXALINE DERIVATIVE; 3 CHLORO 2 (METHYLTHIO); 3 CHLORO 2 (METHYLTHIO)QUINOXALINE DERIVATIVE; 4 [(2 CHLORO 6 METHYLPHENYL)AMINO] 7,8 DIMETHOXYIMIDAZO[1,5 A]QUINOXALINE; BMS 238497; ETHYL ISOCYANOACETATE; IMIDAZO[1,5 A]QUINOXALINE 3 CARBOXYLIC ACID; PROTEIN TYROSINE KINASE INHIBITOR; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; ROOM TEMPERATURE; STEREOCHEMISTRY;

CARBOXYLIC ACIDS; CHLORINE; IMIDAZOLES; ISOCYANATES; METHYLATION; MOLECULAR STRUCTURE; QUINOXALINES; SULFHYDRYL COMPOUNDS; SULFUR;

EID: 34250864992     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070590k     Document Type: Article

References (29)

1. (a) Campiani, G.; Morelli, E.; Gemma, S.; Nacci, V.; Butini, S.; Hamon, M.; Novellino, E.; Greco, G.; Cagnotto, A.; Goegan, M.; Cervo, L.; Valle, F. D.; Fracasso, C.; Caccia, S.; Mennini, T. J. Med. Chem. 1999, 42, 4362.
2. (a) Ohmori, J.; Shimizu-Sasamata, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1997, 40, 2053.
3. (b) Deleuze-Masquéfa, C.; Gerebtzoff, G.; Subra, G.; Fabreguettes, J.-R.; Ovens, A.; Carraz, M.; Strub, M.-P.; Bompart, J.; George, P.; Bonnet, P.-A. Biorg. Med. Chem. 2004, 12, 1129.
4. (c) Parra, S.; Laurent, F.; Subra, G.; Deleuze-Masquéfa, C.; Benezech, V.; Fabreguettes, J.-R.; Vidal, J.-P.; Pocock, T.; Elliott, K.; Small, R.; Escale, R.; Michel, A.; Chapat, J.-P.; Bonnet, P.-A. Eur. J. Med. Chem. 2001, 36, 255.
5. Chen, B.-C.; Zhao, R.; Bednarz, M. S.; Wang, B.; Sundeen, J. E.; Banish, J. C. J. Org. Chem. 2004, 69, 977 and references therein.
6. Sarges, R.; Howard, H. R.; Browne, R. G.; Lebel, L. A.; Seymour, P. A.; Koe, B. K. J. Med. Chem. 1990, 33, 2240.
7. Unciti-Broceta, A.; Pineda-de-las-Infantas, J.; Diaz-Mochón, J. J.; Romagnoli, R.; Baraldi, P. G.; Gallo, M. A.; Espinosa, A. J. Org. Chem. 2005, 70, 2878.
8. Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. J. Med. Chem. 1995, 38, 1330.
9. Jon Jacobsen, E.; Stelzer, L. S.; Belonga, K. L.; Carter, D. B.; Im, W. B.; Sethy, V. H.; Tang, A. H.; VonVoigtlander, P. F.; Petke, J. D. J. Med. Chem. 1996, 39, 3820.
10. Davey, D. D.; Erhardt, P. W.; Cantor, E. H.; Greenberg, S. S.; Ingebretsen, W. R.; Wiggins, J. J. Med. Chem. 1991, 34, 2671.
11. Colotta, V.; Cecchi, L.; Catarzi, D.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. Eur. J. Med. Chem. 1995, 30, 133.
12. Tenbrink, R. E.; Jacobsen, E. J.; Gammill, R. B. U.S. Patent 5541324, July 30, 1996; Chem. Abstr. 1996, 125, 195687.
13. Hansen, H. C.; Frank, W. EP 344943 A1, Dec 6, 1989; Chem. Abstr. 1990, 112, 216962.
14. Lee, T. D.; Brown, R. E. U.S. Patent 4440929, April 3, 1984; Chem. Abstr. 1984, 101, 7202.
15. Banish, J. C.; Chen, P.; Das, J.; Iwanowicz, E. J.; Norris, D. J.; Padmanaba, R.; Roberge, J. Y.; Schieven, G. L. U.S. Patent 6235740, May 22, 2001.
16. Chen, P.; Norris, D.; Iwanowicz, E. J.; Spergel, S. H.; Lin, J.; Gu, H. H.; Shen, Z.; Wityak, J.; Lin, T.-A.; Pang, S.; De Fex, H. F.; Pitt, S.; Shen, D. R.; Doweyko, A. M.; Bassolino, D. A.; Roberge, J. Y.; Poss, M. A.; Chen, B.-C.; Scheiven, G. L.; Banish, J. C. Bioorg. Med. Chem. Lett. 2002, 12, 1361.
17. Norris, D.; Chen, P.; Banish, J. C.; Das, J.; Moquin, R.; Chen, B.-C.; Guo, P. Tetrahedron Lett. 2001, 42, 4297.
18. Chen, P.; Banish, J. C.; Iwanowicz, E.; Lin, J.; Bednarz, M. S.; Chen, B.-C. Tetrahedron Lett. 2001, 42, 4293.
19. Review: (a) Ila, H.; Junjappa, H.; Mohanta, P. K. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist T. L., Eds.; Pergamon: New York, 2001; Vol. 13, Chapter 1, p 1.
20. (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
21. Recent papers: (a) Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 10030.
22. (b) Peruncheralathan, S.; Yadav, A. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 9644.
23. (c) Panda, K.; Venkatesh, C.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2005, 2045.
24. (d) Sundaram, G. S. M.; Venkatesh, C.; Syam, Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2004, 69, 5760.
25. (e) Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. Tetrahedron 2004, 60, 3457.
26. (f) Mahata, P. K.; Venkatesh, C.; Syam, Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3966.
27. (g) Panda, K.; Suresh, J. R.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3498.
28. Venkatesh, C.; Singh, B.; Mahata, P. K.; Ila, H.; Junjappa, H. Org. Lett. 2005, 7, 2169.
29. For the substituent effect on 2,3-dichloroquinoxalines, see: Ford, E.; Brewster, A.; Jones, G.; Bailey, J.; Sumner, N. Tetrahedron Lett. 2000, 41, 3197.