Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

Tetrahedron

Volumn 62, Issue 35, 2006, Pages 8398-8403

  Gangadasu, B ^a   Narender, P ^a   Bharath Kumar, S ^a   Ravinder, M ^a   Ananda Rao, B ^a   Ramesh, Ch ^a   China Raju, B ^a   Jayathirtha Rao, V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Chloronicotinaldehydes; Diphosgene triphosgene; Enamides; Mechanism; Selectivity; Vilsmeier reaction

Indexed keywords

ACETAMIDE DERIVATIVE; ALDEHYDE DERIVATIVE; CHLORONICOTINALDEHYDE DERIVATIVE; ORGANOPHOSPHATE; PHOSGENE; PYRIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; VILSMEIER REAGENT;

ARTICLE; CHEMICAL REACTION; CONCENTRATION RESPONSE; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; VILSMEIER REACTION;

EID: 33745964623     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.026     Document Type: Article

References (33)

1. Jones G. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 5 (1996), Pergamon, Oxford 167
2. Balasubramanian M., and Keay J.G. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 5 (1996), Pergamon, Oxford 245
3. Gavin D.H. Tetrahedron 60 (2004) 6043
4. Bailey T.D., Goe G.L., and Scriven E.F.V. Chem. Heterocycl. Compd. 14 (1984) 1
5. Thummel R.P. Chem. Heterocycl. Compd. 14 (1984) 253
6. Kumar R., and Chandra R. Adv. Heterocycl. Chem. 78 (2001) 269
7. Hanket T., Brunne R.M., Miller H., and Reichel F. Angew. Chem., Int. Ed. 38 (1999) 643
8. Marson C.M. Tetrahedron 48 (1992) 3659
9. Meth-Cohn O. Heterocycles 35 (1993) 539
10. Guzman A., Ronero M., Maddox M.L., and Machowski J.M. J. Org. Chem. 55 (1990) 5793
11. Sreenivasulu M., and Krishna Rao G.S. Indian J. Chem., Sect. B 28 (1989) 584
12. Mahata P.K., Venkatesh C., Syam Kumar U.K., Ila H., and Junjappa H. J. Org. Chem. 68 (2003) 3966
13. Chupp J.P., and Metz S. J. Heterocycl. Chem. 16 (1979) 65
14. Katrtizky A.R., and Arend M. J. Org. Chem. 63 (1998) 9989
15. Amaresh R.R., and Perumal P.T. Synth. Commun. 30 (2000) 2269
16. Meth-Cohn O., and Westwood K.T. J. Chem. Soc., Perkin Trans. 1 (1984) 1173
17. Gigou A., Beaucourt J.P., Lellouche J.P., and Gree R. Tetrahedron Lett. 32 (1991) 635
18. Caijo F., Mosset P., Gree R., Bouchez V.A., Boutin J., Renard P., Caignard D.H., and Dacquet C. Bioorg. Med. Chem. Lett. (2005) 4421
19. China Raju, B.; Jayathirtha Rao, V. U.S. Patent 6,565,528, 2003;
20. Gangadasu B., Palaniappan S., and Jayathirtha Rao V. Synlett (2004) 1285
21. Gangadasu B., Narender P., China Raju B., and Jayathirtha Rao V. J. Chem. Res. 7 (2004) 480
22. Gangadasu B., Narender P., China Raju B., and Jayathirtha Rao V. Indian J. Chem., Sect. B 45 (2006) 1259
23. Narender P., Gangadasu B., China Raju B., and Jayathirtha Rao V. Synth. Commun. 34 (2004) 1097
24. Srinivas K., Srinivas U., Jayathirtha Rao V., Bhanu prakash K., Hara Kishore B., and Murthy U.S.N. Bioorg. Med. Chem. Lett. 15 (2005) 1121
25. Cambell K.N., Sommers A.H., and Cambell B.K. J. Am. Chem. Soc. 66 (1944) 82
26. Breederveld H. Recl. Trav. Chim. Pays-Bas 79 (1960) 401
27. Burk M.J., Casy G., and Johnson N.B. J. Org. Chem. 63 (1998) 6084
28. Zhu G., Chen Z., and Zhang X. J. Org. Chem. 64 (1999) 6907
29. Vogel's Textbook of Practical Organic Chemistry. 4th ed. (1978), London, Longman p 501
30. Hardy P.J., Kerrin S.L., and Manatt S.L. J. Org. Chem. 38 (1973) 4196
31. Kolar A.J., and Olsen R.K. Synthesis (1977) 457
32. Srinivasan A., Stephenson R.W., and Olsen R.K. J. Org. Chem. 42 (1977) 2256
33. Reihard, L. W. U.S. Patent 5,304,651, 1994.