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One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate.

ABSTRACT: A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating ?-(het)aroyl-?-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular O-arylation, furnishing the 2-(het)aryl/alkyl-3-cyanobenzofurans in high yields. A probable mechanism for the base-induced cleavage of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles to ?-(het)aroyl-?-(2-bromoaryl)acetonitriles in the presence of benzyl carbamate has been proposed.

SUBMITTER: Saraiah B

PROVIDER: S-EPMC6644376 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate.

Saraiah Bonagiri B Gautam Vibha V Acharya Anand A Pasha Mohamed Afzal MA Ila Hiriyakkanavar H

ACS omega 20180726 7

A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating α-(het)aroyl-α-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular <i>O</i>-arylation, furnishing the 2-(het)aryl/alkyl-3-cyanobenzofurans in high yields. A probable mechanism for the base-induced cleavage of 2-(2-bromoaryl)-3-(het)aryl ...[more]

PMID: 31458967

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