Beta-Acylvinyl Anion and Dianion Equivalents: Lithiation of 1-[(2EZ)-3-Chloroprop-2-enyl]-1H-1,2,3-benzotriazole: Preparation and Elaboration of 1-(2-Oxiranylvinyl)-1H-benzotriazoles
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University of Canterbury. Chemistry.
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2004
Authors
Katritzky, A.R.
Manju, K.
Gromova, A.V.
Steel, P.J.
Abstract
The allyllithium, generated from 1-[(2EZ)-3-chloroprop-2-enyl]-1H-1,2,3-benzotriazole (5) and LDA in the presence of HMPA, reacts with enolizable and nonenolizable carbonyls solely at the CCl terminus to give 1-(2-oxiranylvinyl)benzotriazoles 6a−g in 61−82% yields. Allyllithiums generated from 6a,c reacted exclusively at the CBt terminus to give 10a−d in 68−88% yields. Acidic hydrolysis of (oxiranylvinyl)benzotriazoles 6a−g and 10a−d provided 4-hydroxyalk-2- en-1-one derivatives 12a−c,e,g, 13a−d and furan 14 in 41−86% yields.
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Katritzky, A.R., Manju, K., Gromova, A.V., Steel, P.J. (2004) Beta-Acylvinyl Anion and Dianion Equivalents: Lithiation of 1-[(2EZ)-3-Chloroprop-2-enyl]-1H-1,2,3-benzotriazole: Preparation and Elaboration of 1-(2-Oxiranylvinyl)-1H-benzotriazoles. Journal of Organic Chemistry, 69, pp. 6018-6023.