Regioselective syntheses of functionalized 2-aminopyridines and 2-pyridinones through nucleophile-induced ring transformation reactions

Synlett

Volumn , Issue 4, 2005, Pages 623-626

  Goel, Atul ^a   Singh, Fateh V ^a   Sharon, Ashoke ^a   Maulik, Prakas R ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

2 aminopyridine; 2 pyranone; 2 pyridinone; Ring transformation reaction; Urea

Indexed keywords

2 AMINOPYRIDINE DERIVATIVE; 2 PYRIDONE DERIVATIVE; 3 CARBOMETHOXY 4 METHYLSULFANYL 2H PYRAN 2 ONE DERIVATIVE; 3 CYANO 4 METHYLSULFANYL 2(1H)PYRIDINONE; 3 CYANO 4 METHYLSULFANYL 2H PYRAN 2 ONE DERIVATIVE; 4 METHYLSULFANYLPYRIDINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; UREA;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; HYDROGEN BOND; MELTING POINT; MOLECULAR RECOGNITION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 15444378960     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862365     Document Type: Article

References (47)

1. C.D.R.I. Communication No. 6544.
2. (a) Smith, D. In Comprehensive Organic Chemsitry, Vol. 4; Sames, P. G., Ed.; Pergamon: Oxford, 1979, 3.
3. (b) Bailey, T.; Goe, G.; Scriven, E. In Heterocyclic Compounds, Part 5, Vol. 14; Newkome, G. R., Ed.; Wiley: New York, 1984, 215.
4. (c) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives, Vol. 3; Pelletier, S. W., Ed.; Wiley: New York, 1985, 1-90.
5. (a) Spivak, D. A.; Shea, K. J. Anal. Chim. Acta 1999, 435, 4627.
6. (b) Kròl, I.; Rospenk, M.; Sobczyk, L. J. Mol. Struct. 2000, 552, 312.
7. (c) Sugeta, H. Bull. Chem. Soc. Jpn. 1981, 54, 3706.
8. Niño, A.; Muñoz-Caro, C.; Carbö-Dorca, R.; Gironés, X. Biophys. Chem. 2003, 104, 417.
9. Sata, N.; Shibata, T.; Jitsuoka, M.; Ohno, T.; Takahashi, T.; Hirohashi, T.; Kanno, T.; Iwaasa, H.; Kanatani, A.; Fukami, T. Bioorg. Med. Chem. Lett. 2004, 14, 1761.
10. Carlsson, C.; Rosen, I.; Nilsson, E. Acta Anaesthesiol. Scand. 1993, 27, 87.
11. (a) Curran, D.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863.
12. (b) Schultz, A. Chem. Rev. 1973, 73, 385.
13. (c) Kelly, T.; Bell, S.; Osashi, N.; Armstrong-Chong, J. J. Am. Chem. Soc. 1988, 110, 6471.
14. (a) Cox, R.; O'Hagan, D. J. Chem. Soc., Perkin Trans. 1 1991, 2537.
15. (b) Rigby, J.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224.
16. Williams, D.; Lowder, P.; Gu, Y.-G. Tetrahedron Lett. 1997, 38, 327.
17. Teshima, Y.; Shin-ya, K.; Shimazu, A.; Furihota, K.; Chul, H. S.; Furihata, K.; Hayakawa, Y.; Nagai, K.; Seto, H. J. Antibiot. 1991, 44, 685.
18. Matyus, P.; Kasztreiner, E.; Diesler, E.; Behr, A.; Varga, I.; Kosary, J.; Rabloczky, G.; Jaszlits, L. Arch. Pharm. 1994, 327, 543.
19. Narusevicius, E.; Garaliene, V.; Krauze, A.; Duburs, G. Khim. Farm. Zh. 1989, 23, 1459.
20. (a) Tieckelmann, H. In Heterocyclic Compounds, Pyridine and its Derivatives, Supplement Part 3; Abramovitch, R. A., Ed.; Wiley-Intersciences: New York, 1974, 597.
21. (b) Murray, T.; Zimmerman, S. Tetrahedron Lett. 1995, 36, 7627.
22. (a) Sakurai, A.; Midorikawa, H. Bull. Chem. Soc. Jpn. 1968, 41, 430.
23. (b) Latif, N.; Girgis, N. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981, 20, 147.
24. (a) Vorbrüggen, H. Adv. Heterocycl. Chem. 1990, 49, 117.
25. (b) Matsumoto, K.; Minatogawa, H.; Munakata, M.; Toda, M.; Tsukube, H. Tetrahedron Lett. 1990, 27, 3923.
26. (c) Matsumoto, K.; Hashimoto, S.; Otani, S. J. Chem. Soc., Chem. Commun. 1991, 306.
27. (a) McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: New York, 1984, 67.
28. (b) McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: New York, 1984, 460-463.
29. Farhanullah Agarwal, N.; Goel, A.; Ram, V. J. J. Org. Chem. 2003, 68, 2983.
30. Katritzky, A. R.; Belyakov, S. A.; Sorochinsky, A. E.; Henderson, S. A.; Chen, J. J. Org. Chem. 1997, 62, 6210.
31. (a) Decker, H. Chem. Ber. 1892, 25, 443.
32. (b) Mohrle, H.; Weber, H. Tetrahedron 1970, 26, 2953.
33. Jones, G. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: New York, 1984, 395.
34. Rastogi, R. R.; Kumar, A.; Ila, H.; Junjappa, H. J. Chem. Soc., Perkin Trans. 1 1978, 549.
35. Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387.
36. Brun, E. M.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273.
37. Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973.
38. (a) Ram, V. J.; Goel, A. Chem. Lett. 1997, 10, 1021.
39. (b) Nath, M.; Srivastava, P.; Goel, A.; Ram, V. J. Eur. J. Org. Chem. 1998, 2083.
40. (c) Srivastava, P.; Saxena, A. S.; Ram, V. J. Synthesis 2000, 544.
41. (d) Ram, V. J.; Srivastava, P. Curr. Org. Chem. 2001, 5, 571.
42. (a) Tominaga, Y.; Ushirogouchi, A.; Matsuda, Y.; Kobayashi, G. Chem. Pharm. Bull. 1984, 32, 3384.
43. (b) Tominaga, Y.; Ushirogouchi, A.; Matsuda, Y. J. Heterocycl. Chem. 1987, 24, 1557.
44. (c) Ram, V. J.; Verma, M.; Hussaini, F. A.; Shoeb, A. J. Chem. Res., Synop. 1991, 98.
45. (d) Ram, V. J.; Hussaini, F. A.; Singh, S. K.; Shoeb, A. J. Chem. Res., Synop. 1993, 110.
46. 3-hexane (1:1) as eluent.
47. 13NOS: C, 67.50; H, 5.66; N, 6.06. Found: C, 67.62; H, 5.69; N, 6.18.