Tin(IV) chloride selectively promotes the nucleophilic attack of methyl acetoacetate to the cyano instead of the olefinic carbon atom of alpha,beta-unsaturated nitriles to give enaminoketoesters. In the presence of an excess of ketoester a second C-C bond formation occurs followed by cyclisation affording substituted pyridines in a selective cascade sequence. (C) 2002 Elsevier Science Ltd. All rights reserved.
One pot synthesis of unsaturated enaminoketoesters or of pyridines in the tin(IV) chloride-promoted reactions of beta-ketoesters with of alpha,beta-unsaturated nitriles / A. Veronese, C. F. Morelli, M. Basato. - In: TETRAHEDRON. - ISSN 0040-4020. - 58:48(2002), pp. 9709-9712.
One pot synthesis of unsaturated enaminoketoesters or of pyridines in the tin(IV) chloride-promoted reactions of beta-ketoesters with of alpha,beta-unsaturated nitriles
C. F. MorelliSecondo
;
2002
Abstract
Tin(IV) chloride selectively promotes the nucleophilic attack of methyl acetoacetate to the cyano instead of the olefinic carbon atom of alpha,beta-unsaturated nitriles to give enaminoketoesters. In the presence of an excess of ketoester a second C-C bond formation occurs followed by cyclisation affording substituted pyridines in a selective cascade sequence. (C) 2002 Elsevier Science Ltd. All rights reserved.Pubblicazioni consigliate
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