Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds

Tetrahedron

Volumn 58, Issue 49, 2002, Pages 9793-9799

  Demir, Ayhan S ^a   Akhmedov, Idris M ^a   Sesenoglu, Özge ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Cyclization; Enamine esters; Nitrogen heterocycles; Pyrroles

Indexed keywords

2 (2 BROMOALLYL)CYCLOHEXANE 1,3 DIONE; CARBONYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0037010759     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01298-X     Document Type: Article

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31. The mechanism of the deacetylation process leading to the formation of 8 as minor product is uncertain. We suggest that this process works via either an oxidation-decarboxylation reaction, see: (a) Barton D.H.R., Pradhan S.K., Sternhell S., Templeton J.F. J. Chem. Soc. 1961;255 (b) Rao D.V., Stuber F.A., Ulrich H. J. Org. Chem. 44:1979;456 (c) Bauer D.P., Macomber R.S. J. Org. Chem. 40:1975;1990 (d) Trost B.M., Massoit G.S. J. Am. Chem. Soc. 99:1977;4405. or retroaldol type reaction under basic conditions, see: (e) Gassman P.G., Lumb J.T., Zalar F.V. J. Am. Chem. Soc. 89:1967;946 (f) Davies D.G., Derenberg M., Hodge P. J. Chem. Soc. (C). 1971;455 (g) March J., Plankl W. J. Chem. Soc., Perkin Trans. 1. 1977;460 (h) Jung J.-C., Watkins E.B., Avery M.A. Tetrahedron. 58:2002;3639. The reaction is currently being investigated.
32. The mechanism of the deacetylation process leading to the formation of 8 as minor product is uncertain. We suggest that this process works via either an oxidation-decarboxylation reaction, see: (a) Barton D.H.R., Pradhan S.K., Sternhell S., Templeton J.F. J. Chem. Soc. 1961;255 (b) Rao D.V., Stuber F.A., Ulrich H. J. Org. Chem. 44:1979;456 (c) Bauer D.P., Macomber R.S. J. Org. Chem. 40:1975;1990 (d) Trost B.M., Massoit G.S. J. Am. Chem. Soc. 99:1977;4405. or retroaldol type reaction under basic conditions, see: (e) Gassman P.G., Lumb J.T., Zalar F.V. J. Am. Chem. Soc. 89:1967;946 (f) Davies D.G., Derenberg M., Hodge P. J. Chem. Soc. (C). 1971;455 (g) March J., Plankl W. J. Chem. Soc., Perkin Trans. 1. 1977;460 (h) Jung J.-C., Watkins E.B., Avery M.A. Tetrahedron. 58:2002;3639. The reaction is currently being investigated.
33. The mechanism of the deacetylation process leading to the formation of 8 as minor product is uncertain. We suggest that this process works via either an oxidation-decarboxylation reaction, see: (a) Barton D.H.R., Pradhan S.K., Sternhell S., Templeton J.F. J. Chem. Soc. 1961;255 (b) Rao D.V., Stuber F.A., Ulrich H. J. Org. Chem. 44:1979;456 (c) Bauer D.P., Macomber R.S. J. Org. Chem. 40:1975;1990 (d) Trost B.M., Massoit G.S. J. Am. Chem. Soc. 99:1977;4405. or retroaldol type reaction under basic conditions, see: (e) Gassman P.G., Lumb J.T., Zalar F.V. J. Am. Chem. Soc. 89:1967;946 (f) Davies D.G., Derenberg M., Hodge P. J. Chem. Soc. (C). 1971;455 (g) March J., Plankl W. J. Chem. Soc., Perkin Trans. 1. 1977;460 (h) Jung J.-C., Watkins E.B., Avery M.A. Tetrahedron. 58:2002;3639. The reaction is currently being investigated.
34. The mechanism of the deacetylation process leading to the formation of 8 as minor product is uncertain. We suggest that this process works via either an oxidation-decarboxylation reaction, see: (a) Barton D.H.R., Pradhan S.K., Sternhell S., Templeton J.F. J. Chem. Soc. 1961;255 (b) Rao D.V., Stuber F.A., Ulrich H. J. Org. Chem. 44:1979;456 (c) Bauer D.P., Macomber R.S. J. Org. Chem. 40:1975;1990 (d) Trost B.M., Massoit G.S. J. Am. Chem. Soc. 99:1977;4405. or retroaldol type reaction under basic conditions, see: (e) Gassman P.G., Lumb J.T., Zalar F.V. J. Am. Chem. Soc. 89:1967;946 (f) Davies D.G., Derenberg M., Hodge P. J. Chem. Soc. (C). 1971;455 (g) March J., Plankl W. J. Chem. Soc., Perkin Trans. 1. 1977;460 (h) Jung J.-C., Watkins E.B., Avery M.A. Tetrahedron. 58:2002;3639. The reaction is currently being investigated.
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