Bromine-induced facile synthesis of butenolides and spirobutenolides from sterically congested tetrasubstituted dialkyl alkylidene succinates

Synthesis

Volumn , Issue 7, 2010, Pages 1188-1194

  Patel, Ramesh M ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Alkylidene succinates; Bromine; Butenolides; Intramolecular cyclizations; Spirobutenolides

Indexed keywords

ALKYLIDENE SUCCINATES; ALKYLIDENES; BUTENOLIDES; DEHYDROBROMINATION; FACILE SYNTHESIS; GENERAL APPROACH; INTRAMOLECULAR CYCLIZATIONS; MECHANISTIC ASPECTS; QUATERNARY CARBON; REGIO-SELECTIVE; STERICALLY CONGESTED;

CYCLIZATION;

BROMINE;

BROMINE; BUTENOLIDE; SPIRO COMPOUND; SPIROBUTENOLIDE DERIVATIVE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77949851036     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1219233     Document Type: Article

References (28)

1. Rao Y S., Chem. Rev. 1976 76 625
2. Avetisyan A A., Dangyan M T., Russ. Chem. Rev. 1977 46 643
3. Figadre B, Acc. Chem. Res. 1995 28 359
4. Braa M F., Garca M L., Lpez B, de Pascual-Teresa B, Ramos A, Pozuelo J M., Domnguez M T., Org. Biomol. Chem. 2004 2 1864
5. Seitz M, Reiser O, Curr. Opin. Chem. Biol. 2005 9 285
6. Nauen R, Bretschneider T, Elbert A, Fischer R, Tiemann R, Pestic. Outlook 2003 (December) 243
7. Jiang Y.-Q, Shi Y.-L, Shi M, J. Am. Chem. Soc. 2008 130 7202
8. Boukouvalas J, Loach R P., J. Org. Chem. 2008 73 8109
9. Boto A, Hernndez D, Hernndez R, J. Org. Chem. 2008 73 5287
10. Yamaguchi A, Matsunaga S, Shibasaki M, Org. Lett. 2008 10 2319
11. Lebel H, Parmentier M, Org. Lett. 2007 9 3563
12. Hyde A M., Buchwald S L., Org. Lett. 2009 11 2663; and references cited therein
13. Geraghty N W. A., Hernon E M., Tetrahedron Lett. 2009 50 570
14. Zhao Y.-M, Gu P, Tu Y.-Q, Fan C.-A, Zhang Q, Org. Lett. 2008 10 1763
15. Greco G E., Gleason B L., Lowery T A., Kier M J., Hollander L B., Gibbs S A., Worthy A D., Org. Lett. 2007 9 3817
16. Ma S, Lu L, Lu P, J. Org. Chem. 2005 70 1063
17. Robertson J, Meo P, Dallimore J W. P., Doyle B M., Hoarau C, Org. Lett. 2004 6 3861
18. Yoneda E, Kaneko T, Zhang S.-W, Onitsuka K, Takahashi S, Org. Lett. 2000 2 441
19. Harrowven D C., Hannam J C., Tetrahedron 1999 55 9341
20. Haval K P., Argade N P., J. Org. Chem. 2008 73 6936
21. Wakchaure P B., Easwar S, Puranik V G., Argade N P., Tetrahedron 2008 64 1786
22. Baag M M., Puranik V G., Argade N P., J. Org. Chem. 2007 72 1009
23. Thomas C J., Wolak M A., Birge R R., Lees W J., J.Org.Chem. 2001 66 1914
24. Gupta G, Banerjee S, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1990 29 787
25. Asiri A M., Salem A.-J S., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999 38 488
26. Lee W.-W W., Gan L.-M, Loh T.-P, Synlett 2005 2473
27. Paris J, Gouet E, Payard M, Reboul-Salze S, Hartmann L, Tronche P, Eur. J. Med. Chem. 1982 17 563; and references cited therein
28. Ballini R, Bosica G, Damianl M, Righi P, Tetrahedron 1999 55 13451