The first one-pot, solvent-free microwave-accelerated, three- componentsynthesis of spirothiazolidin-4-ones via Staudinger/aza-Wittig coupling/cyclization

Helvetica Chimica Acta

Volumn 95, Issue 6, 2012, Pages 922-928

  Ponnuswamy, Alagusundaram ^a   Shanmugavelan, Poovan ^a   Nagarajan, Sangaraiah ^a   Sathishkumar, Murugan ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ONE POT; ORGANIC AZIDES; SHORT REACTION TIME; SOLVENT FREE; THREE-COMPONENT;

BIOCHEMISTRY; CHEMISTRY;

SOLVENTS;

4 BENZYL 8 (TERT BUTYL) 1 THIA 4 AZASPIRO[4.5]DECAN 3 ONE; 4 BENZYL 8 PHENYL 1 THIA 4 AZASPIRO[4.5]DECAN 3 ONE; AZIDE; ETHYL 2 (3 OXO 1 THIA 4 AZASPIRO[4.5]DEC 4 YL)ACETATE; ETHYL 2 (3 OXO 8 PHENYL 1 THIA 4 AZASPIRO[4.5]DEC 4 YL)ACETATE; ETHYL 2 (7 METHYL 3 OXO 1 THIA 4 AZASPIRO[4.5]DEC 4 YL)ACETATE; ETHYL 2 [8 (TERT BUTYL) 3 OXO 1 THIA 4 AZASPIRO[4.5]DEC 4 YL]ACETATE; METHYL 2 (3 OXO 1 THIA 4 AZASPIRO[4.5]DEC 4 YL)ACETATE; METHYL 2 (3 OXO 8 PHENYL 1 THIA 4 AZASPIRO[4.5]DEC 4 YL)ACETATE; METHYL 2 (7 METHYL 3 OXO 1 THIA 4 AZASPIRO[4.5]DEC 4 YL)ACETATE; METHYL 2 [8 (TERT BUTYL) 3 OXO 1 THIA 4 AZASPIRO[4.5]DEC 4 YL]ACETATE; SPIROTHIAZOLIDIN 4 ONE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STAUDINGER REACTION; WITTIG REACTION;

EID: 84862568414     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201100441     Document Type: Article

References (32)

1. K. Takahashi, B. Witkop, A. Brossi, M. A. Maleque, E. X. Albuquerque, Helv. Chim. Acta 1982, 65, 252.
2. J. Kobayashi, M. Tsuda, K. Agemi, H. Shigemori, M. Ishibashi, T. Sasaki, Y. Mikami, Tetrahedron 1991, 47, 6617.
3. D. M. James, H. B. Kunze, D. J. Faulkner, J. Nat. Prod. 1991, 54, 1137.
4. G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 2000, 100, 1741.
5. A. Verma, S. K. Saraf, Eur. J. Med. Chem. 2008, 43, 897.
6. T. Srivastava, W. Haq, S. B. Katti, Tetrahedron 2002, 58, 7619.
7. A. Dandia, R. Singh, K. Arya, Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 551.
8. S. K. Sahu, S. K. Mishra, M. Banerjee, P. K. Panda, P. K. Misro, J. Indian Chem. Soc. 2006, 83, 725.
9. A. Dandia, R. Singh, S. Khaturia, C. Mérienne, G. Morgant, A. Loupy, Bioorg. Med. Chem. 2006, 14, 2409.
10. B. O. Kasimogullari, Z. Cesur, Molecules 2004, 9, 894.
11. S. K. Srivastava, S. L. Srivastava, S. D. Srivastava, J. Indian Chem. Soc. 2000, 77, 104.
12. R. C. Sharma, D. Kumar, J. Indian Chem. Soc. 2000, 77, 492.
13. R. K. Rawal, T. Srivastava, W. Haq, S. B. Katti, J. Chem. Res. 2004, 5, 368.
14. H. Chen, J. Bai, L. Zhao, X. G. Yuan, X. L. Li, K. Q. Cao, Chin. J. Org. Chem. 2008, 28, 1092.
15. Z.-Z. Zhou, W. Huang, F.-Q. Ji, M.-W. Ding, G.-F. Yang, Heteroatom Chem. 2007, 18, 381.
16. J. Fraga-Dubreuil, J. P. Bazureau, Tetrahedron 2003, 59, 6121.
17. H. Wamhoff, G. Richardt, S. Stöben, Adv. Heterocycl. Chem. 1995, 64, 159;
18. P. M. Fresneda, P. Molina, Synlett 2004, 1;
19. S. Eguchi, Arkivoc 2005, (ii), 98;
20. S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem., Int. Ed. 2005, 44, 5188;
21. S. Eguchi, in 'Topics in Heterocyclic Chemistry', Vol. 6, 2006, p. 113;
22. F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, J. M. De los Santos, Tetrahedron 2007, 63, 523;
23. S. P. Marsden, A. E. McGonagle, B. McKeever-Abbas, Org. Lett. 2008, 10, 2589;
24. D. R. Bobeck, S. France, C. A. Leverett, F. Sánchez-Cantalejo, A. Padwa, Tetrahedron Lett. 2009, 50, 3145.
25. M. Sathishkumar, P. Shanmugavelan, S. Nagarajan, M. Maheswari, M. Dinesh, A. Ponnuswamy, Tetrahedron Lett. 2011, 52, 2830;
26. M. Sathishkumar, S. Nagarajan, P. Shanmuga Velan, M. Dinesh, A. Ponnuswamy, J. Braz. Chem. Soc. 2011, 22, 2065.
27. S. Nagarajan, P. Shanmugavelan, M. Sathishkumar, N. Priyadharshini, P. Sudakar, A. Ponnuswamy, Synth. Commun. doi: 10.1080/00397911.2011.606043.
28. M. Sathishkumar, K. Palanikumar, A. Mariappan, S. Archana, A. Ponnuswamy, J. Iran. Chem. Soc. (Accepted. Ms. No.: OM-11-718-14).
29. M. F. El-Zohry, I. M. A. Awad, A. A. Abdel-Hafez, A. Ali, Arch Pharm. 1993, 326, 115.
30. L. S. Campbell-Verduyn, L. Mirfeizi, R. A. Dierckx, H. P. Elsinga, B. L. Feringa, Chem. Commun. 2009, 2139.
31. P. Roy, M. Boisvert, Y. Leblanc, Org. Synth. 2007, 84, 262.
32. C. E. McKenna, B. A. Kashemirov, K. M. Błażewska, I. Mallard-Favier, C. A. Stewart, J. Rojas, M. W. Lundy, F. H. Ebetino, R. A. Baron, J. E. Dunford, M. L. Kirsten, M. C. Seabra, J. L. Bala, M. S. Marma, M. J. Rogers, F. P. Coxon, J. Med. Chem. 2010, 53, 3454.