✦ LIBER ✦

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

✍ Scribed by Vishnu Ji Ram; Nidhi Agarwal

Book ID: 104231533
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 112 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01481-2

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✦ Synopsis

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 a source of the carbanion, in moderate yield.

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