Use of the curtius rearrangement of acryloyl azides in the synthesis of 3,5-disubstituted pyridines: Mechanistic studies

Journal of Organic Chemistry

Volumn 75, Issue 19, 2010, Pages 6625-6630

  Chuang, Ta Hsien ^a   Chen, Yu Chi ^b   Pola, Someshwar ^c  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b VANUNG UNIVERSITY   (Taiwan)

^c KAKATIYA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLOYL AZIDE; ARYL GROUP; DOUBLE BONDS; MECHANISTIC STUDIES; PYRIDINE DERIVATIVES; SYNTHETIC APPROACH;

ACETIC ACID; NITROGEN COMPOUNDS; PH EFFECTS;

PYRIDINE;

2 (2 METHOXYLBENZYL) 3,5 BIS (2 METHOXYLPHENYL) PYRIDINE; 2 (3 METHOXYBENZYL) 3,5 BIS (3 METHOXYPHENYL) PYRIDINE; 2 (4 METHOXYBENZYL) 3,5 BIS (4 METHOXYPHENYL) PYRIDINE; 2 BENZYL 3,5 DIPHENYLPYRIDINE; 2 BUTOXYMETHYL 5 BUTOXYPYRIDINE; 2 BUTYL 3,5 DIPROPYLPYRIDINE; 3,5 BIS (2 NITROPHENYL) PYRIDINE; 3,5 BIS (3 METHOXYPHENYL) PYRIDINE; 3,5 BIS (3 NITROPHENYL) PYRIDINE; 3,5 BIS (4 METHOXYLPHENYL) PYRIDINE; 3,5 BIS (4 NITROPHENYL) PYRIDINE; 3,5 BIS (ETHOXYCARBONYL) PYRIDINE; 3,5 BIS (PYRIDINE 3 YL) PYRIDINE; 3,5 DIPHENYLPYRDINE; 3,5 DIPHENYLPYRIDINE 2 ONE; 3,5 DIPROPYLPYRIDINE; 4 BENZYL 5 PHENYL 3,4 DIHYDRO 1H PYRIMIDIN 2 ONE; ACETIC ACID; ACRYLOYL AZIDE; AZIDE; CARBON 13; CINNAMOYL AZIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CURTIUS REARRANGEMENT; CYCLOADDITION; SYNTHESIS;

ACETIC ACID; AZIDES; CYCLIZATION; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM;

EID: 77957139470     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101394c     Document Type: Article

References (41)

1. Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5, pp 245 - 300.
2. Spitzner, D. In Science of Synthesis; Black, D. St. C., Ed.; Thieme: Stuttgart, 2004; pp 11 - 284.
3. Fraser, H. L.; Hopper, D. W.; Kutterer, K. M. K.; Crombie, A. L. In Progress In Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Elsevier: Amsterdam, 2008; Vol. 19, pp 314 - 352.
4. Hopper, D. W.; Kuterer, K. M. K.; Crombie, A. L.; J. J. Clemens. In Progress In Heterocyclic Chemistry; Gribble, G. W., Joule, J. A. Elsevier: Amsterdam, 2009; Vol. 20, pp 289 - 332.
5. Tagat, J. R.; McCombie, S. W.; Barton, B. E.; Jackson, J.; Shortall, J. Bioorg. Med. Chem. Lett. 1995, 5, 2143-2146
6. Kumar, A.; Rhodes, R. A.; Spychala, J.; Wilson, W. D.; Boykin, D. W.; Tidwell, R. R.; Dykstra, C. C.; Hall, J. E.; Jones, S. K.; Schinazi, R. F. Eur. J. Med. 'hem. 1995, 30, 99-106
7. Durinda, J.; Szücs, L.; Struhavova, L.; Kolencs, J.; Heger, J. Cesk. Farm. 1972, 21, 276-282
8. Attia, A.; Abo-Ghalia, M. H.; El-Salam, O. I. Abd. Pharmazie 1995, 50, 455-459
9. Eliel, E. L.; McBride, R. T.; Kaufmann, S. J. Am. Chem. Soc. 1953, 75, 4291-4296
10. Panzella, L.; Donato, P. D.; Comes, S.; Napolitano, A.; Palumbo, A.; dIschia, M. Tetrahedron Lett. 2005, 46, 6457-6460
11. Burns, N. Z.; Baran, P. S. Angew. Chem., Int. Ed. 2008, 47, 205-208
12. Winter, A.; Risch, N. Synthesis 2003, 2667-2670
13. Komatsu, M.; Ohgishi, H.; Takamatsu, S.; Ohshiro, Y.; Agawa, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 213-214
14. Ohta, K.; Iwaoka, J.; Kamijo, Y.; Okada, M.; Nomura, Y. Nippon Kagaku Kaishi 1989, 1593-1600
15. Vijn, R. J.; Arts, H. J.; Green, R.; Castelijns, A. M. Synthesis 1994, 573-578
16. Balasubrahmanyam, S. N.; Jeyashri, B.; Namboothiri, I. N. N. Tetrahedron 1994, 50, 8127-8142
17. Couve-Bonnaire, S.; Carpentier, J. -F.; Mortreux, A.; Castanet, Y. Tetrahedron 2003, 59, 2793-2799
18. Liu, Y.; Khemtong, C.; Hu, J. Chem. Commun. 2004, 398-399
19. Berthiol, F.; Kondolff, I.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2004, 689, 2786-2798
20. Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283-5286
21. Jacquemard, U.; Routier, S.; Dias, N.; Lansiaux, A.; Goossens, J.-F.; Bailly, C.; Mérour, J.-Y. Eur. J. Med. Chem. 2005, 40, 1087-1095
22. Kuhnert, N.; Patel, C.; Jami, F. Tetrahedron Lett. 2005, 46, 7575-7579
23. Li, J. H.; Zhang, Y. H.; Song, R. J.; Xie, Y. X.; Deng, C. L.; Liang, Y. Synthesis 2007, 2957-2966
24. Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251-7254
25. Chuang, T. H.; Wu, P. L. J. Chin. Chem. Soc. 2006, 53, 413-420
26. Farley, C. P.; Eliel, E. L. J. Am. Chem. Soc. 1956, 78, 3477-3481
27. Jeyashri, B.; Balasubrahmanyam, S. N. Indian J. Chem., Sect. B 1985, 24, 341-349
28. Hano, Y.; Shimazaki, M.; Nomura, T.; Ueda, S. Heterocycles 1999, 50, 989-994
29. Fry, A. J. Am. Chem. Soc. 1953, 75, 2686-2688
30. Lenz, G. R. Synthesis 1978, 489-518
31. Ulrich, H. Acc. Chem. Res. 1969, 2, 186-192
32. Abdulla, R. F.; Fuhr, K. H. J. Med. Chem. 1975, 18, 625-627
33. Komatsu, M.; Takamatsu, S.; Uesaka, M.; Yamamoto, S.; Ohshiro, Y. J. Org. Chem. 1984, 49, 2691-2699
34. Tišler, M.; Stanovnik, B. J. Chem. Soc., Chem. Commun. 1980, 313-314
35. Taylor, R. J. Chem. Soc., Perkin Trans. 2 1983, 89-95
36. Gopinath, K. W.; Govindachari, T. R.; Nagarajan, K.; Purushothaman, K. K. J. Chem. Soc. 1957, 1144-1148
37. Brown, D. J.; England, B. T. Aust. J. Chem. 1970, 23, 625-627
38. Ishikura, M.; Ohta, T.; Terashima, M. Chem. Pharm. Bull. 1985, 33, 4755-4763
39. Dieterich, D. Synthesis 1972, 631-632
40. Folkers, K.; Johnson, J. B. J. Am. Chem. Soc. 1933, 55, 3361-3368
41. Hirai, K.; Matsuda, H.; Kishida, Y. Chem. Pharm. Bull. 1973, 21, 1090-1095