An efficient one-pot synthesis of spiro dihydrofuran oxindole and spiro 2-hydroxytetrahydrofuran oxindole derivatives via (3+2) oxidative cycloaddition mediated by CAN

Tetrahedron Letters

Volumn 48, Issue 16, 2007, Pages 2943-2947

  Savitha, G ^a   Niveditha, S K ^a   Muralidharan, D ^a   Perumal, P T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYTETRAHYDROFURAN OXINDOLE DERIVATIVE; AMMONIUM NITRATE; CARBONYL DERIVATIVE; FURAN DERIVATIVE; OXINDOLE; SPIRO COMPOUND; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ONE POT SYNTHESIS; OXIDATION;

EID: 33947246504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.045     Document Type: Article

References (46)

1. For selected reviews, see:. Sannigrahi M. Tetrahedron 55 (1999) 9007
2. Heathcock C.H., Graham S.L., Pirrung M.C., Plavac F., and White C.T. Spirocyclic Systems. In: ap Simon J. (Ed). The Total Synthesis of Natural Products Vol. 5 (1983), John Wiley and Sons, New York 264
3. For reviews, see:. Williams R.M., and Cox R.J. Acc. Chem. Res. 36 (2003) 127
4. Da Silva J.F.M., Garden S.J., and Pinto A.C. J. Braz. Chem. Soc. (2001) 273
5. He Y., Jiang T., Kuhen K.L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya B., Tuntland T., Zhang K., and Karanewsky D. Bioorg. Med. Chem. Lett. 16 (2006) 2109
6. Pajouhesh H., Parsons R., and Popp F.D. J. Pharm. Sci. 72 (1983) 318
7. Skiles J.W., and McNeil D. Tetrahedron Lett. 31 (1990) 7277
8. Fokas D., Ryan W.J., Casebier D.S., and Coffen D.L. Tetrahedron Lett. 39 (1998) 2235
9. Ganguly A.K., Seah N., Popov V., Wang C.H., Kuang R., Saksena A.K., Pramanik B.N., Chan T.M., and McPhail A.T. Tetrahedron Lett. 43 (2002) 8981
10. Grigg R., Millington E.L., and Thonton-Pett M. Tetrahedron Lett. 43 (2002) 2605
11. Syam Kumar U.K., Lla H., and Junjappa H. Org. Lett. 3 (2001) 4193
12. Nair V., Vellath S., Poonath M., Mohan R., and Suresh E. Org. Lett. 8 (2006) 507
13. Nair V., Biju A.T., Vinod A.U., and Suresh E. Org. Lett. 7 (2005) 5139
14. Grigg R., Putnikovic B., and Urch C.J. Tetrahedron Lett. 37 (1996) 695
15. Beccalli E.M., Clerici F., and Gelmi M.L. Tetrahedron 59 (2003) 4615
16. Jayashankaran J., Rathna Durga R., Venkatesan R., and Raghunathan R. Tetrahedron 61 (2005) 5595
17. Melikyan G.G. Synthesis (1993) 833
18. Iqbal J., Bhatia B., and Nayyar N.K. Chem. Rev. 94 (1994) 519
19. Baciocchi E., and Ruzziconi R. J. Org. Chem. 56 (1991) 4772
20. Nair V., Mathew J., and Radhakrishnan K.V. J. Chem. Soc., Perkin Trans. 1 (1996) 1487 and references cited therein
21. Pirrung M.C., and Lee Y.R. J. Am. Chem. Soc. 117 (1995) 4814
22. Yoshida J.-I., Yano S., Ozawa T., and Kawobata N. J. Org. Chem. 50 (1985) 3467
23. Onitsuka S., Nishino H., and Kurosawa K. Tetrahedron Lett. 41 (2000) 3149
24. Onitsuka S., Nishino H., and Kurosawa K. Heterocycl. Commun. 6 (2000) 529
25. Onitsuka S., Nishino H., and Kurosawa K. Tetrahedron 59 (2003) 755
26. Corey E.J., and Cheng X.-M. The Logic of Chemical Synthesis (1989), Wiley, New York
27. Nicolaou K.C., and Sorensen E.J. Classics in Total Synthesis (1996), VCH, Weinheim
28. In: Eicher T., and Hauptmann S. (Eds). The Chemistry of Heterocycles. 2nd ed. (2003), Wiley, New York
29. Merino P., Franco S., Merchan F.L., and Tejero T. Recent Research Developments in Synthetic Organic Chemistry Vol. 3 (2000), Transworld Research Network, Kerala 65
30. Garofola A.W., Litvak J., Wang L., Dubenko L.G., Cooper R., and Bierer D.E. J. Org. Chem. 64 (1999) 3369
31. Schoop A., Greiving H., and Gohrt A. Tetrahedron Lett. 41 (2000) 1913
32. Kajikawa S., Nishino H., and Kuroosawa K. Heterocycles 54 (2001) 171
33. Jogo S., Nishino H., Yasutake M., and Shinmyozu T. Tetrahedron Lett. 43 (2002) 903
34. Alcaide B., Almendros P., and Rodriguez-Acebes R. J. Org. Chem. 71 (2006) 2346
35. 3: C, 70.67; H, 5.44; N, 3.43%. Found: C, 70.68; H, 5.42; N, 3.40%.
36. Gayathri D., Velmurugan D., Ravikumar K., Savitha G., and Perumal P.T. Acta Cryst. E63 (2007) o846-o848
37. Reid A.M., and Steel P.G. J. Chem. Soc., Perkin Trans. 1 (1998) 2795
38. Bessmertnykh A., Henin F., and Muzart J. Carbohydr. Res. 339 (2004) 1377
39. Tiwari P., and Misra A.K. Tetrahedron Lett. 47 (2006) 3573
40. Miyazawa M., Hirose Y., Narantsetseg M., Yokoyama H., Yamaguchi S., and Hirai Y. Tetrahedron Lett. 45 (2004) 2883
41. Cicchillo R.M., and Norris P. Carbohydr. Res. 328 (2000) 431
42. Bragnier N., and Scherrmann M.-C. Synthesis 5 (2005) 814
43. Borrachero P., Cabrera-Escribano F., Gomez-Guillen M., and Vogel P. Synlett 1 (2006) 45
44. Auvin, S.; Chabrier De Lassauniere, P.-E. FR. Patent 2863268A1, 2005; Chem. Abstr. 2005, 143, 44075d.
45. Gayathri D., Velmurugan D., Ravikumar K., Savitha G., and Perumal P.T. Acta Cryst. E62 (2006) o5947-o5949
46. Gayathri D., Velmurugan D., Ravikumar K., Savitha G., and Perumal P.T. Acta Cryst. E63 (2007) o1034-o1036