Novel four-component approach for the synthesis of polyfunctionalized 1,4-dihydropyridines in aqueous media

Helvetica Chimica Acta

Volumn 94, Issue 3, 2011, Pages 382-388

  Hadjebi, Melika ^a   Hashtroudi, Mehri S ^b   Bijanzadeh, Hamid Reza ^c   Balalaie, Saeed ^a  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b Iranian National Center for Oceanography   (Iran)

^c TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS MEDIA; AROMATIC ALDEHYDE; CATALYTIC AMOUNTS; COMPONENT APPROACHES; DIHYDROPYRIDINES; DIMETHYL ACETYLENEDICARBOXYLATE; MALONONITRILES; PROPANEDINITRILE; ROOM TEMPERATURE;

ALDEHYDES;

SYNTHESIS (CHEMICAL);

1,4 DIHYDROPYRIDINE DERIVATIVE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALDEHYDE; CADMIUM CHLORIDE; DIMETHYL 6 AMINO 1 BENZYL 4 (4 BROMOPHENYL) 5 CYANO 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 1 BENZYL 4 (4 CHLOROPHENYL) 5 CYANO 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 1 BENZYL 5 CYANO 1,4 DIHYDRO 4 (3 HYDROXYPHENYL)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 1 BENZYL 5 CYANO 1,4 DIHYDRO 4 (3 NITROPHENYL)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 1 BENZYL 5 CYANO 1,4 DIHYDRO 4 (4 NITROPHENYL)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 1 BENZYL 5 CYANO 1,4 DIHYDRO 4 PHENYLPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 1 BENZYL 5 CYANO 4 (4 CYANOPHENYL) 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL BUT 2 YNEDIOATE; MALONONITRILE; PHOSPHORIC ACID; PROPANEDINITRILE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; MASS SPECTROMETRY; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 79952713942     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000228     Document Type: Article

References (38)

1. A. Dömling, I. Ugi, Angew. Chem., Int. Ed. 2000, 39, 3168;
2. A. Dömling, Chem. Rev. 2006, 106, 17;
3. A. Dömling, in 'Multicomponent Reactions', Ed. Wiley - VCH, Weinheim, 2005, pp. 76-94;
4. L. F. Tietze, Chem. Rev. 1996, 96, 115.
5. D. J. Triggle, D. A. Langs, R. A. Janis, Med. Res. Rev. 1989, 9, 123;
6. T. Takenaka, O. Inagaki, M. Terai, M. Asano, K. Kubo, J. Pharmacol. Exp. Ther. 1988, 244, 699;
7. S. Visentin, B. Rolando, A. Di Stilo, R. Fruttero, M. Novara, E. Carbone, C. Roussel, N. Vanthuyne, A. Gasco, J. Med. Chem. 2004, 47, 2688.
8. M. Richter, J. Molnár, A. Hilgeroth, J. Med. Chem. 2006, 49, 2838;
9. A. Hilgeroth, U. Baumeister, F.W. Heinemann, Eur. J. Org. Chem. 2000, 245.
10. S. Goldmann, J. Stoltefuss, Angew. Chem., Int. Ed. Engl. 1991, 30, 1559;
11. D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223.
12. A. Sausins, G. Duburs, Heterocycles 1988, 27, 269.
13. A. Hantzsch, Chem. Ber. 1881, 14, 1637;
14. U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1.
15. T. Chennat, U. Eisner, J. Chem. Soc., Perkin Trans. 1 1975, 926;
16. S. Balalaie, E. Kowsari, Monatsh. Chem. 2001, 132, 1551.
17. M. J. Khoshkholgh, M. Lotfi, S. Balalaie, F. Rominger, Tetrahedron 2009, 65, 4228;
18. M. J. Khoshkholgh, S. Balalaie, H. R. Bijanzadeh, F. Rominger, J. H. Gross, Tetrahedron Lett. 2008, 49, 6965;
19. M. J. Khoshkholgh, S. Balalaie, H. R. Bijanzadeh, J. H. Gross, Arkivoc 2009, ix, 114;
20. M. J. Khoshkholgh, S. Balalaie, S. H. R. Bijanzadeh, J. H. Gross, Synlett 2009, 55;
21. M. Bararjanian, S. Balalaie, F. Rominger, S. Barouti, Helv. Chim. Acta 2010, 93, 777;
22. S. Balalaie, S. Abdolmohammadi, B. Soleimanifard, Helv. Chim. Acta 2009, 92, 932;
23. M. Bararjanian, S. Balalaie, F. Rominger, B. Movassagh, H. R. Bijanzadeh, J. Org. Chem. 2010, 75, 2806;
24. M. Bararjanian, S. Balalaie, B. Movassagh, H. R. Bijanzadeh, Tetrahedron Lett. 2010, 51, 3277.
25. L. J. Goossen, M. Arndt, M. Blanchot, F. Rudolphi, F. Menges, G. Nieder-Schattenburg, Adv. Synth. Catal. 2008, 350, 2701, and refs. cit. therein.
26. J. I. Dickstein, S. I. Miller, in 'The Chemistry of Functional Groups', 'The Chemistry of Carbon- Carbon Triple Bonds', Part 2, Ed. S. Patai, Wiley, Chichester, 1978, Chapt. 19, pp. 813;
27. R. Huisgen, K. Herbig, A. Siegel, H. Huber, Chem. Ber. 1966, 99, 2526;
28. R. Naitoh, Y. Nakamura, E. Katano, Y. Nakamura, E. Okada, M. Asaoka, Heterocycles 2004, 63, 1009;
29. J. P. Bouillon, B. Tinant, J. M. Nuzillard, C. Portella, Synthesis 2004, 711;
30. J. E. Dolfini, J. Org. Chem. 1965, 30, 1298;
31. A. K. Ogawa, C. Willoughby, R. Bergeron, K. P. Ellsworth, W. M. Geissler, R.W. Myers, J. Yao, G. Harris, K. T. Chapmann, Bioorg. Med. Chem. Lett. 2003, 13, 3405;
32. A. Ziayaei-Halimehjani, M. R. Saidi, Tetrahedron Lett. 2008, 49, 1244.
33. I. Yavari, S. Souri, Synlett 2007, 2969;
34. I. Yavari, S. Souri, Synlett 2008, 1208.
35. I. Yavari, A. Hossein-Nia, Magn. Reson. Chem. 1994, 30, 413;
36. I. Yavari, A. Shaabani, H. Soleimani, F. Nourmohammadian, H. R. Bijanzadeh, Magn. Reson. Chem. 1996, 34, 1003;
37. K. Herbig, R. Huisgen, H. Huber, Chem. Ber. 1966, 99, 2546
38. Q. Zhu, H. Jiang, J. Li, M. Zhang, X. Wang, C. Qi, Tetrahedron 2009, 65, 4604.