Synthesis and Reduction of 2,2-diaryl-1-nitroethylenes by using a chiral and a non chiral NADH model in the pyrrolopyridine series

Journal of Heterocyclic Chemistry

Volumn 33, Issue 4, 1996, Pages 1211-1215

  Levacher, Vincent ^a   Valque, Claude ^a   Coupa, Sophie ^a   Dupas, Georges ^a   Quéguiner, Guy ^a   Bourguignon, Jean ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2842548091     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330435     Document Type: Article

References (31)

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29. It should be noted that compound 4 could not be detected when reagent 2a or sodium borohydride were used. Compound 4 does not result from elimination of nitrous acid of compound 7 as proved by a blank experiment performed with compound 7 in the presence of reagent 2b (leq) and magnesium perchlorate (2 equivalents) (acetonitrile/60°/two days). It can thus be assumed that compound 4 is obtained either by reduction of 2-(2-pyridyl)-2-phenyl-1-nitroethylene 5 or by elimination of nitrous acid of the initial reduction intermediate; N. Ono, R. Tamura, and A. Kaji, J. Am. Chem. Soc. 102, 2851 (1980).
30. We assume that a large amount of magnesium perchlorate would promote the formation of 2-benzoylpyridine. Transformation of 2,2-diaryl-1-nitroethanes into diaryl ketones has already been observed under the influence of Lewis acids; A. D. Grebenyuk, R. Kh. Pulatov, and G. G. Rybnikova, Translated from Zhumal Organicheskoi Khimii, 12, 1590 (1976).
31. Reduction of conjugated nitroalkenes with sodium borohydride and NADH models may be accompanied by the formation of polynitroalkanes. For futher details see ref [8b]; [9]; B. C. Ranu, and R. Chakraborty, Tetrahedron, 48, 5317 (1992).