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

[Image: see text] 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 s...

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Autores principales: Saraiah, Bonagiri, Gautam, Vibha, Acharya, Anand, Pasha, Mohamed Afzal, Ila, Hiriyakkanavar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644376/
https://www.ncbi.nlm.nih.gov/pubmed/31458967
http://dx.doi.org/10.1021/acsomega.8b01172
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author Saraiah, Bonagiri
Gautam, Vibha
Acharya, Anand
Pasha, Mohamed Afzal
Ila, Hiriyakkanavar
author_facet Saraiah, Bonagiri
Gautam, Vibha
Acharya, Anand
Pasha, Mohamed Afzal
Ila, Hiriyakkanavar
author_sort Saraiah, Bonagiri
collection PubMed
description [Image: see text] 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 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 α-(het)aroyl-α-(2-bromoaryl)acetonitriles in the presence of benzyl carbamate has been proposed.
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spelling pubmed-66443762019-08-27 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 Gautam, Vibha Acharya, Anand Pasha, Mohamed Afzal Ila, Hiriyakkanavar ACS Omega [Image: see text] 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 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 α-(het)aroyl-α-(2-bromoaryl)acetonitriles in the presence of benzyl carbamate has been proposed. American Chemical Society 2018-07-26 /pmc/articles/PMC6644376/ /pubmed/31458967 http://dx.doi.org/10.1021/acsomega.8b01172 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Saraiah, Bonagiri
Gautam, Vibha
Acharya, Anand
Pasha, Mohamed Afzal
Ila, Hiriyakkanavar
One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate
title One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate
title_full One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate
title_fullStr One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate
title_full_unstemmed One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate
title_short One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate
title_sort one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans from 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and benzyl carbamate
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644376/
https://www.ncbi.nlm.nih.gov/pubmed/31458967
http://dx.doi.org/10.1021/acsomega.8b01172
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