Unusual mechanistic pathway for the synthesis of novel spiro-oxindoles via 3-phenyl-5-isoxazolone ring cleavage by secondary amino acids

Tetrahedron Letters

Volumn 52, Issue 27, 2011, Pages 3437-3442

  Lakshmi, Neelakandan Vidhya ^a   Arun, Yuvaraj ^a   Perumal, Paramasivam T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

3 Phenyl 5 isoxazolone; Isatin; l Proline; Multicomponent reaction; Sarcosine; Spiro oxindoles

Indexed keywords

3 PHENYL 5 ISOXAZOLONE; AMINO ACID DERIVATIVE; ISATIN; ISOXAZOLE DERIVATIVE; OXINDOLE; PROLINE; SARCOSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 79957935061     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.093     Document Type: Article

References (33)

1. P. Thirumurugan, A. Nandakumar, D. Muralidharan, and P.T. Perumal J. Comb. Chem. 12 2010 161
2. R. Ghahremanzadeh, G.I. Shakibaei, S. Ahadi, and A. Bazgir J. Comb. Chem. 12 2010 191
3. Y. Qian, X. Xu, L. Jiang, D. Prajapati, and W. Hu J. Org. Chem. 75 2010 7483
4. H. Chen, and D. Shi J. Comb. Chem. 12 2010 571
5. Z. Chen, and J. Wu Org. Lett. 12 2010 4856
6. I. Couto, I. Tellitu, and E. Domnguez J. Org. Chem. 75 2010 7954
7. N.V. Lakshmi, P. Thirumurugan, and P.T. Perumal Tetrahedron Lett. 51 2010 1064
8. N.V. Lakshmi, P. Thirumurugan, K.M. Noorulla, and P.T. Perumal Bioorg. Med. Chem. Lett. 20 2010 5054
9. T.J. Donohoe, J.Y.K. Chiu, and R.E. Thomas Org. Lett. 9 2007 421
10. Z. Liu, and A. Nefzi J. Comb. Chem. 12 2010 566
11. Lunsford, C. D.; Cale, A. D.; Dawson, N. D. Brit. Patent 1174419 (1969); Chem. Abstr. 1970, 72, 66822n.
12. D. Quintás, A. Garca, and D. Domnguez Tetrahedron Lett. 44 2003 9291
13. S. Gemma, G. Campiani, S. Butini, E. Morelli, P. Minetti, O. Tinti, and V. Nacci Tetrahedron 58 2002 3689
14. B.S. Kotha, C.A. Deb, and K. Lahiri Synthesis 2 2009 0165
15. T. Augustine, C.C. Kanakam, S.M. Vithiya, and V. Ramkumar Tetrahedron Lett. 50 2009 5906
16. B.M. Trost, and M.K. Brennan Synthesis 18 2009 3003
17. D. Basavaiah, and R.K. Reddy Org. Lett. 9 2007 57
18. R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, and D. Sriram Eur. J. Med. Chem. 44 2009 3821
19. S.T. Hilton, T.C.T. Ho, G. Pljevaljcic, and K. Jones Org. Lett. 2 2000 2639
20. M. Smet, C.V. Oosterwijck, K.V. Hecke, L.V. Meervelt, A. Vandendriessche, and W. Dehaen Synlett 2004 2388
21. G. Cravotto, G.B. Giovenzana, T. Pilati, M. Sisti, and G. Palmisano J. Org. Chem. 66 2001 8447
22. A.R.S. Babu, R. Raghunathan, and S. Baskaran Tetrahedron 65 2009 2239
23. R.S. Kumar, and S. Perumal Tetrahedron Lett. 48 2007 7164
24. N.V. Lakshmi, P. Thirumurugan, and P.T. Perumal Synlett 6 2010 955
25. T.H. Babu, A.A. Joseph, D. Muralidharan, and P.T. Perumal Tetrahedron Lett. 51 2010 994
26. A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, and Sh.M. El-Bady Bioorg. Med. Chem. 12 2004 2483
27. M. González, J.L. Segura, C. Seoane, and N. Martín J. Org. Chem. 66 2001 8872
28. 2O exchangeable).
29. D. Crich, and A.A. Bowers Org. Lett. 9 2007 5323
30. S. Lee, and S. Jung Carbohydr. Res. 339 2004 461
31. 3: C, 68.05; H, 5.11; N, 12.53. Found: C, 68.12; H, 5.18; N, 12.61.
32. Crystallographic data for compound 5e in this paper have been deposited with the Cambridge Crystallographic Data centre as supplemental publication no. CCDC- 805359. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 01223 336033 or email: deposit@ccdc.cam.ac.uk ).
33. 3: C, 63.72; H, 4.58; N, 10.62 found: C, 63.78; H, 4.51; N, 10.71.