The first solvent-free, microwave-accelerated, three-component synthesis of thiazolidin-4-ones via one-pot tandem Staudinger/aza-wittig reaction

Journal of Heterocyclic Chemistry

Volumn 51, Issue 4, 2014, Pages 1004-1011

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

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4 THIAZOLIDINONE DERIVATIVE; AZIDE; ORGANIC COMPOUND; WATER;

ARTICLE; MICROWAVE RADIATION; MOLECULAR LIBRARY; ONE POT SYNTHESIS; SOLUTION AND SOLUBILITY; STAUDINGER REACTION; WITTIG REACTION;

EID: 84905060630     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.1705     Document Type: Article

References (47)

1. Verma, A.,;, Saraf, S. K., Eur J Med Chem 2008, 43, 897.
2. Tanabe, Y.,;, Suzukamo, G.,;, Komuro, Y.,;, Imanishi, N.,;, Morooka, S.,;, Enomoto, M.,;, Kojima, A.,;, Sanemitsu, Y.,;, Mizutani, M., Tetrahedron Lett 1991, 32, 379.
3. Liu H.-L.,;, Li Z.,;, Anthonsen T.,. Molecules 2000, 5, 1055.
4. Kato, T.,;, Ozaki, T.,;, Ohi, N., Tetrahedron Asymmetry 1999, 10, 3963.
5. Previtera, T.,;, Vigorita, M. G.,;, Bisila, M.,;, Orsini, F.,;, Benetolla, F.,;, Bombieri, G., Eur J Med Chem 1994, 29, 317.
6. Balzarini, J.,;, Orzeszko, B.,;, Maurin, J. K.,;, Orzeszko, A., Eur J Med Chem 2007, 42, 993.
7. Knutsen, L. J. S.,;, Hobbs, C. J.,;, Earnshaw, C. G., Bioorg Med Chem Lett 2007, 17, 662.
8. Mujeebur Rahman, V. P.,;, Mukhtar, S.,;, Ansari, W. H., Eur J Med Chem 2005, 40, 173.
9. Look, G. C.,;, Schullek, J. R.,;, Homes, C. P.,;, Chinn, J. P.,;, Gordon, E. M.,;, Gallop, M. A., Bioorg Med Chem Lett 1996, 6, 707.
10. Barreca, M. L.,;, Chimirri, A.,;, Luca, L. D.,;, Monforte, A.,;, Monforte, P.,;, Rao, A.,;, Zappala, M.,;, Balzarini, J.,;, De Clercq, E.,;, Pannecouque, C.,;, Witvrouw, M., Bioorg Med Chem Lett 2001, 1793.
11. (a), Brown, C. F., Chem Rev 1961, 61, 463
12. (b), Singh, S. P.,;, Parmar, S. S.,;, Raman, K.,;, Stenberg, V. I., Chem Rev 1981, 81, 175.
13. (a), Gududuru, V.,;, Nguyen, V.,;, Dalton, J. T.,;, Miller, D. D., Synlett 2004, 13, 2357
14. (b), Cesur, Z.,;, Guner, H.,;, Otuk, G., Eur J Med Chem 1994, 29, 981
15. (c), Vicini, P.,;, Geronikaki, A.,;, Anastasia, K.,;, Incertia, M.,;, Zania, F., Bioorg Med Chem 2006, 14, 3859
16. (d), Ottana, R.,;, Maccari, R.,;, Barreca, M. L.,;, Bruno, G.,;, Rotondo, A.,;, Rossi, A.,;, Chiricosta, G.,;, Di Paola, R.,;, Sautebin, L.,;, Cuzzocread, S.,;, Vigorita, M. G., Bioorg Med Chem 2005, 13, 4243
17. (e), Holmes, C. P.,;, Chinn, J. P.,;, Look, G. C.,;, Gordon, E. M.,;, Gallop, M. A., J Org Chem 1995, 60, 7328
18. (f), Anderluh, M.,;, Jukic, M.,;, Petric, R., Tetrahedron 2009, 65, 344
19. (g), Cunico, W.,;, Gomes, C. R. B.,;, Ferreira, L. G.,;, Capri, L. R.,;, Soares, M.,;, Wardell, S. M. S. V., Tetrahedron Lett 2007, 48, 6217
20. (h), de Vries, A. H. M.,;, Hof, R. P.,;, Staal, D.,;, Kellogg, R. M.,;, Feringa, B. L., Tetrahedron Asymmetry 1997, 8, 1539.
21. Srivastava, S. K.,;, Srivastava, S. L.,;, Srivastava, S. D., J Indian Chem Soc 2000, 77, 104.
22. Sharma, R. C.,;, Kumar, D., J Indian Chem Soc 2000, 77, 492.
23. Srivastava, T.,;, Haq, W.,;, Katti, S. B., Tetrahedron 2002, 58, 7619.
24. Rawal, R. K.,;, Srivastava, T.,;, Haq, W.,;, Katti, S. B., J Chem Res 2004, 5, 368.
25. Chen, H.,;, Bai, J.,;, Zhao, L.,;, Yuan, X. G.,;, Li, X. L.,;, Cao, K. Q., Chin J Org Chem 2008, 28, 1092.
26. (a), Zhou, Z. Z.,;, Huang, W.,;, Ji, F. Q.,;, Ding, M. W.,;, Yang, G. F., Heteroat Chem. 2007, 18, 381
27. (b), Dandia, A.,;, Singh, R.,;, Khaturia, S.,;, Mérienne, C.,;, Morgant, G.,;, Loupy, A., Bioorg Med Chem 2006, 14, 2409
28. (c), Fraga-Dubreuil, J.,;, Bazureau, J. P., Tetrahedron 2003, 59, 6121.
29. (a), Wamhoff, H.,;, Richardt, G.,;, Stölben, S., Adv Heterocycl Chem 1995, 64, 159
30. (b), Fresneda, P. M.,;, Molina, P.,; Synlett 2004, 15, 1
31. (c), Eguchi, S.,. Arkivoc 2005, 2, 98
32. (d), Brase, S.,;, Gil, C.,;, Knepp, K.,;, Zimmermann, V., Angew Chem Int Ed 2005, 44, 5188
33. (e), Eguchi, S.,. Heterocycl Chem 2006, 6, 113
34. (f), Palacios, F.,;, Alonso, C.,;, Aparicio, D.,;, Rubiales, G.,;, De los Santos, J. M., Tetrahedron 2007, 63, 523
35. (g), Fuwa, H.,;, Okamura, Y.,;, Morohashi, Y.,;, Tomita, T.,;, Iwatsubo, T.,;, Kan, T.,;, Fukuyama, T.,;, Natsugari, H., Tetrahedron Lett 2004, 45, 2323
36. (h), Marsden, S. P.,;, McGonagle, A. E.,;, McKeever-Abbas, B., Org Lett 2008, 10, 2589.
37. Chen, H.,;, Zhang, H.,;, Feng, J.,;, Li, X.,;, Jiao, L.,;, Qin, Z.,;, Yin, Q.,;, Zhang, J., Eur J Org Chem 2009, 6100.
38. Shen, F.,;, Li, X.,;, Zhang, X.,;, Yin, Q.,;, Qin, Z.,;, Chen, H.,;, Zhaipu Mac, J. Z., Org Biomol Chem DOI: 10.1039/c1ob05675a.
39. (a), Sathishkumar, M.,;, Shanmuga velan, P.,;, Nagarajan S.,;, Maheswari, M.,;, Dinesh, M.,;, Ponnuswamy, A., Tetrahedron Lett 2011, 52, 2830
40. (b), Sathishkumar, M.,;, Nagarajan, S.,;, Shanmuga velan, P.,;, Dinesh, M.,;, Ponnuswamy, A., J Braz Chem Soc 2011, 22, 2065.
41. Nagarajan, S.,;, Shanmugavelan, P.,;, Sathishkumar, M.,;, Priyadharshini, N.,;, Sudakar, P.,;, Ponnuswamy, A., Synth Commun DOI: 10.1080/00397911.2011. 606043.
42. Sathishkumar, M.,;, Palanikumar, K.,;, Mariappan, A.,;, Archana, S.,;, Ponnuswamy, A., J. Iran Chem. Soc. DOI: 10.1007/s13738-012-0090-7.
43. Fun, H. K.,;, Hemamalini, M.,;, Shanmugavelan, P.,;, Ponnuswamy, A.,;, Jagatheesan, R., Acta Cryst 2011, E67, o2706.
44. Tierney, J.,;, Sheridan, D.,;, Kovalesky, K.,;, Mascavage, L. M.,;, Schneider, K.,;, Sheely, C., Heterocycl Commun 2000, 2, 105.
45. Raval, B. K.,;, Trivedi, J. J., J Indian Chem Soc 1960, 37, 353.
46. Lingampalle, D.,;, Jawale, D.,;, Waghmare, R.,; Mane. R. Synth Commun 2010, 40, 2397.
47. Bolognese, A.,;, Correale, G.,;, Manfra, M.,;, Lavecchia, A.,;, Novellino, E.,;, Barone, V., Org Biomol Chem 2004, 2, 2809.