Iodo cyclofunctionalization of 2,4-dialkenyl-1,3-dicarbonyl compounds: Synthesis of substituted 3-(2-furylidene)-2-furanones

Journal of Heterocyclic Chemistry

Volumn 39, Issue 4, 2002, Pages 639-644

  Valduga, Claudete J ^a   Stefani, Hélio A ^a   Petragnani, Nicola ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DICARBONYL DERIVATIVE; 3 [5 (1 IODOETHYL)TETRAHYDRO 2 FURYLIDENE] 5 IODOMETHYLTETRAHYDRO 2 FURANONE; 5 (1 IODOETHYL) 3 (7 IODOPERHYDROBENZO[B] 2 FURYLIDENE)TETRAHYDRO 2 FURANONE; 5 (1 IODOETHYL) 3 [5 (1 IODOETHYL)TETRAHYDRO 2 FURYLIDENE]TETRAHYDRO 2 FURANONE; 5 IODOMETHYL 3 (5 IODOMETHYLTETRAHYDRO 2 FURYLIDENE)TETRAHYDRO 2 FURANONE; 5 IODOMETHYL 3 (7 IODOPERHYDROBENZO[B] 2 FURYLIDENE)TETRAHYDRO 2 FURANONE; 7 IODO 3 (5 IODOMETHYLTETRAHYDRO 2 FURYLIDENE)PERHYDROBENZO[B] 2 FURANONE; 7 IODO 3 (7 IODOPERHYDROBENZO[B] 2 FURYLIDENE)PERHYDROBENZO[B] 2 FURANONE; 7 IODO 3 [5 (1 IODOETHYL)TETRAHYDRO 2 FURYLIDENE]PERHYDROBENZO[B] 2 FURANONE; CARBONYL DERIVATIVE; CHLOROFORM; FURANONE DERIVATIVE; IODINE; SODIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0036666307     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570390406     Document Type: Article

References (16)

1. D. L. J. Clive, G. Chitattu, N. Curtis, W. A. Kiel and C. K., Wong, J. Chem. Soc., Chem. Commun., 725, (1977).
2. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 734 (1976).
3. G. Cardillo and M. Orena, Tetrahedon, 46, 3321 (1990) and references cited therein.
4. C. Galli, G. Illuminati, L Mandolini and P. Tamborra, J. Am. Chem. Soc., 99, 2591 (1977).
5. H. A. Stefani, N. Petragnani, C. J. Valduga and C. A. Brandt, Tetrahedron Lett., 38, 4977 (1997); see also Corrigendum in Tetrahedron Lett., 39, 7624 (1998).
6. H. A. Stefani, N. Petragnani, C. J. Valduga and C. A. Brandt, Tetrahedron Lett., 38, 4977 (1997); see also Corrigendum in Tetrahedron Lett., 39, 7624 (1998).
7. S. D. Richnovsky and P. A. Bartlett, J. Am. Chem. Soc., 103, 3963 (1981).
8. P. A. Bartlett and P. C. Ting, J. Org. Chem., 51, 2230 (1986).
9. V. Jagër and H. J. Günther, Tetrahedron Lett., 2543 (1977).
10. A. R. Chamberlin, R. L. Mulholland Jr, S. D. Kahn and W.J. Hehre, J. Am. Chem. Soc., 109, 672 (1987) and references cited therein.
11. L. F. P. Amaral and S. C. Melo, J. Org. Chem., 38, 800 (1973).
12. [11a] R. B. Turner and R. H. Garner, J. Am. Chem. Soc., 79, 253 (1957);
13. [11b] R. B. Turner and R. H. Garner, J. Am. Chem. Soc., 80, 1424 (1958).
14. J. Klein, J. Am. Chem. Soc., 81, 364 (1959);
15. [11b] H. O. House, R. G. Carlson and H. Babad, J. Org. Chem., 28, 3359 (1963).
16. J. Zukerman-Schpector, H. A. Stefani, C. J. Valduga, C. A. Brandt and I. Caracelli, Z. Kristallogr., 213, 733 (1998).