Carbanion-induced base-catalyzed synthesis of unsymmetrical biaryls from suitably functionalized, 2H-pyran-2-ones through ring-transformation reactions

A synthesis of unsymmetrical highly functionalized biaryls with an amino substituent juxtaposed with two nitrile groups in one of the Phenyl rings is delineated and illustrated by the carbanion-induced ring-transformation of 6-aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitrile (1) and 4-sec-amino-6...

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 40; pp. 7127 - 7129
Main Authors Ram, VJ, Agarwal, N
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.10.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
SIGMA-LIGANDS
CROSS-COUPLING REACTION
ACIDS
CONVERSION
LIGNANS
ARYL
DERIVATIVES
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Summary:A synthesis of unsymmetrical highly functionalized biaryls with an amino substituent juxtaposed with two nitrile groups in one of the Phenyl rings is delineated and illustrated by the carbanion-induced ring-transformation of 6-aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitrile (1) and 4-sec-amino-6-aryl-2H-pyran-2-one-3-carbonitrile (2) to 2-amino-4-aryl-6-methylsulfanyl-1,3-benzodinitrile (3) and 2-amino-6-sec-amino-4-aryl-1,3-benzodinitrile (4) using malononitrile as it source of the carbanion, in moderate yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(01)01481-2