A mild and efficient procedure for the conversion of aromatic carboxylic esters to secondary amides

Canadian Journal of Chemistry

Volumn 83, Issue 8, 2005, Pages 1137-1140

  Arora, Revika ^a   Paul, Satya ^a   Gupta, Rajive ^a  

^a UNIVERSITY OF JAMMU   (India)

Author keywords

Aromatic carboxylic esters; Aromatic primary amines; Microwave activation; Secondary amides; Zn dust

Indexed keywords

AMINES; CARBOXYLIC ACIDS; DISTILLATION; MICROWAVE HEATING; ORGANIC SOLVENTS;

AROMATIC CARBOXYLIC ESTERS; AROMATIC PRIMARY AMINES; MICROWAVE ACTIVATION; SECONDARY AMINES; ZN DUST;

ESTERS;

AMIDE; AROMATIC AMINE; AROMATIC COMPOUND; CARBOXYLIC ACID DERIVATIVE; ESTER; HYDROCHLORIC ACID; WATER; ZINC;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEATING; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 28944433951     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-134     Document Type: Article

References (36)

1. W.-C. Chou, C.-W. Tan, S.-F. Chen, and H. Ku. J. Org. Chem. 63, 10015 (1998).
2. (a) J. March. In Advanced organic chemistry. 4th ed. John Wiley and Sons, New York. 1992. pp. 417-425;
3. (b) A. Vogel. In Textbook of practical organic chemistry. Longman Scientific and Technical and Wiley, New York. 1989. pp. 708-710;
4. G.V.M. Sharma, T. Shekharam, and V. Upender. Tetrahedron, 46. 5665 (1990).
5. S.-T. Chen, S.-H. Wu, and K.-T. Wang. Synthesis, 37 (1989).
6. K.V.N.S. Sriniwas and B. Das. J. Org. Chem. 68, 1165 (2003).
7. J. Cossy and C. Pale-Grosdemange. Tetrahedron Lett. 30, 2771 (1989).
8. T.-H. Chan and L.T.L. Wong. J. Org. Chem. 34, 2766 (1969).
9. K. Dendrinos, J. Jeong, W. Huang, and A.G. Kalivretenos. Chem. Commun. 499 (1998).
10. K.S. Keshavamurthy, Y.D. Vankar, and D.N. Dhar. Synthesis, 506 (1982).
11. H.W. Grimmel, A. Guenther, and J.F. Morgan. J. Am. Chem. Soc. 68, 539 (1946).
12. (a) H. Yazawa, K. Tanaka, and K. Kariyone. Tetrahedron Lett. 15, 3995 (1974);
13. (b) W.-B. Wang and E.J. Roskamp. J. Org. Chem. 57, 6101 (1992);
14. W.-B. Wang, J.A. Restituyo, and E.J. Roskamp. Tetrahedron Lett. 34, 7217 (1993).
15. (a) G.M. Strunz and H. Finlay. Tetrahedron, 50, 11 113 (1994);
16. (b) N. Raju, K. Ramalingam, and D.P. Nowotnik. Tetrahedron, 48, 10 233 (1992).
17. A.R. Katritzky, H.-Y. He, and K. Suzuki. J. Org. Chem. 65, 8210 (2000), and refs. cited therein.
18. B.C. Ranu and P. Dutta. Synth. Commun. 33, 297 (2003).
19. R.S. Varma and K.P. Naicker. Tetrahedron Lett. 40, 6177 (1999).
20. F.-Z. Zradni, J. Hamelin, and A. Derdour. Synth. Commun. 32, 3525 (2002).
21. L. Perreux, A. Loupy, and M. Delmotte. Tetrahedron, 59, 2185 (2003).
22. (a) J.K. Shorrock, J.H. Clark, K. Wilson, and J. Chisem. Org. Process Res. Dev. 5, 249 (2001);
23. (b) C. Baleizao, A. Corma, H. Garcia, and A. Leyva. Chem. Commun. 606 (2003);
24. E.B. Mobofu, J.H. Clark, and D.J. Macquarrie. Green Chem. 3, 23 (2001).
25. (a) S.D. Burke and R.L. Danheiser. Handbook of reagents for organic syntheis: Oxidizing and reducing agents. John Wiley and Sons, Chichester. 1999. pp. 504-510;
26. (b) M.S.R. Murty, B. Jyothirmai, P.R. Krishna, and J.S. Jadav. Synth. Commun. 33, 2483 (2003);
27. J.S. Yadav, B.V.S. Reddy, G. Kondaji, R.S. Rao, and S.P. Kumar. Tetrahedron Lett. 43, 8133 (2002);
28. Y. Ogawa, A. Saiga, M. Mori, T. Shibata, and K. Takegi. J. Org. Chem. 65, 1031 (2000).
29. S. Paul, P. Nanda, R. Gupta, and A. Loupy. Synthesis, 2877 (2003).
30. S. Paul and M. Gupta. Synthesis, 1789 (2004).
31. S. Paul and M. Gupta. Tetrahedron Lett. 45, 8825 (2004).
32. N.K. Vishnoi. In Advanced practical organic chemistry. 2nd ed. 1996. Vikas Publishing House Pvt. Ltd., New Delhi.
33. V. Joshi, S.S. Jalisatgi, and M.I. Hari. Indian J. Chem. Sect. B, 25B, 83 (1986).
34. T. Jan, D. Floner, and C. Moinet. Electrochim. Acta, 42, 2075 (1997).
35. A.F.M. Fahmy, G. Hosni, and H. Abdel Fadeel. Indian J. Chem. Sect. B, 14B, 871 (1976).
36. A.F.M. Fahmy, N.F. Aly, and M.H. Arief. Indian J. Chem. Sect. B, 16B, 697 (1978).