Three-component reaction of an isocyanide and a dialkyl acetylenedicarboxylate with a phenacyl halide in the presence of water: An efficient method for the one-pot synthesis of γ-iminolactone derivatives

Helvetica Chimica Acta

Volumn 93, Issue 10, 2010, Pages 2033-2036

  Ramazani, Ali ^a   Rezaei, Aram ^a   Mahyari, Amir Tofangchi ^a   Rouhani, Morteza ^a   Khoobi, Mehdi ^a  

^a UNIVERSITY OF ZANJAN   (Iran)

Author keywords

Iminolactones; Acetylenecarboxylates; Green chemistry; Isocyanides; Multicomponent reactions; Phenacyl halides

Indexed keywords

ACETYLENECARBOXYLATES; GREEN CHEMISTRY; ISOCYANIDES; MULTI-COMPONENT REACTIONS; PHENACYL HALIDES;

SYNTHESIS (CHEMICAL);

CYANIDES;

CYANIDE; DICARBOXYLIC ACID; GAMMA IMINOLACTONE DERIVATIVE; LACTONE DERIVATIVE; PHENACYL HALIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; PRIORITY JOURNAL;

EID: 77956213517     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000057     Document Type: Article

References (20)

1. Y. Ito, H. Kato, T. Saegusa, J. Org. Chem. 1982, 47, 741.
2. E. Winterfeldt, D. Schumann, H.-J. Dillinger, Chem. Ber. 1969, 102, 1656.
3. V. Nair, A. U. Vinod, J. S. Nair, A. R. Sreekanth, N. P. Rath, Tetrahedron Lett. 2000, 41, 6675
4. V. Nair, A. U. Vinod, N. Abhilash, R. S. Menon, V. Santhi, R. L. Varma, S. Viji, S. Mathew, R. Srinivas, Tetrahedron 2003, 59, 10279
5. V. Nair, R. S. Menon, A. Deepthi, B. Rema Devi, A. T. Biju, Tetrahedron Lett. 2005, 46, 1337
6. V. Nair, A. Deepthi, Tetrahedron Lett. 2006, 47, 2037.
7. N. Chatani, M. Oshita, M. Tobisu, Y. Ishii, S. Murai, J. Am. Chem. Soc. 2003, 125, 7812.
8. G. Bez, C.-G. Zhao, Org. Lett. 2003, 5, 4991.
9. S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575.
10. S. Ma, H. Xie, Tetrahedron 2005, 61, 251.
11. M. B. Teimouri, A. Shaabani, R. Bazhrang, Tetrahedron 2006, 62, 1845
12. A. Shaabani, E. Soleimani, A. Sarvary, Monatsh. Chem. 2008, 139, 629.
13. I. Yavari, A. Ramazani, A. Yahya-Zadeh, Synth. Commun. 1996, 26, 4495.
14. A. Ramazani, E. Ahmadi, A. R. Kazemizadeh, L. Dolatyari, N. Noshiranzadeh, I. Eskandari, A. Souldozi, Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 2419.
15. A. Ramazani, A. Souldozi, Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2663.
16. A. Souldozi, A. Ramazani, N. Bouslimani, R. Welter, Tetrahedron Lett. 2007, 48, 2617.
17. A. Souldozi, A. Ramazani, Tetrahedron Lett. 2007, 48, 1549.
18. A. R. Kazemizadeh, A. Ramazani, J. Braz. Chem. Soc. 2009, 20, 309.
19. A. Ramazani, A. Tofangchi Mahyari, M. Rouhani, A. Rezaei, Tetrahedron Lett. 2009, 50, 5625.
20. D. D. Perrin, W. L. F. Armarego, 'Purification of Laboratory Chemicals', Pergamon Press, Oxford, U.K., 1988, p.20.