Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(benzylidenamino)benzonitriles with arylboronic acids has been developed. This transformation features good functional group tolerance and provides an alternative synthetic pathway to access 2,4-diarylquinazolines in moder...

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Main Authors: Julin Gong, Kun Hu, Yetong Zhang, Yinlin Shao, Tianxing Cheng, Maolin Hu, Jiuxi Chen
Format: Article
Language:English
Published: MDPI AG 2019-01-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/3/463
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author Julin Gong
Kun Hu
Yetong Zhang
Yinlin Shao
Tianxing Cheng
Maolin Hu
Jiuxi Chen
author_facet Julin Gong
Kun Hu
Yetong Zhang
Yinlin Shao
Tianxing Cheng
Maolin Hu
Jiuxi Chen
author_sort Julin Gong
collection DOAJ
description The first example of the palladium-catalyzed tandem addition/cyclization of 2-(benzylidenamino)benzonitriles with arylboronic acids has been developed. This transformation features good functional group tolerance and provides an alternative synthetic pathway to access 2,4-diarylquinazolines in moderate to good yields. A plausible mechanism for the formation of 2,4-diarylquinazolines involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed.
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spelling doaj.art-f72b04416db44e12aa4d00d1776f1c2b2022-12-22T00:47:03ZengMDPI AGMolecules1420-30492019-01-0124346310.3390/molecules24030463molecules24030463Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of NitrilesJulin Gong0Kun Hu1Yetong Zhang2Yinlin Shao3Tianxing Cheng4Maolin Hu5Jiuxi Chen6College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, ChinaThe first example of the palladium-catalyzed tandem addition/cyclization of 2-(benzylidenamino)benzonitriles with arylboronic acids has been developed. This transformation features good functional group tolerance and provides an alternative synthetic pathway to access 2,4-diarylquinazolines in moderate to good yields. A plausible mechanism for the formation of 2,4-diarylquinazolines involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed.https://www.mdpi.com/1420-3049/24/3/463palladium-catalyzedtandem reactionnitrilecarbopalladationquinazoline
spellingShingle Julin Gong
Kun Hu
Yetong Zhang
Yinlin Shao
Tianxing Cheng
Maolin Hu
Jiuxi Chen
Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles
Molecules
palladium-catalyzed
tandem reaction
nitrile
carbopalladation
quinazoline
title Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles
title_full Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles
title_fullStr Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles
title_full_unstemmed Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles
title_short Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles
title_sort efficient tandem addition cyclization for access to 2 4 diarylquinazolines via catalytic carbopalladation of nitriles
topic palladium-catalyzed
tandem reaction
nitrile
carbopalladation
quinazoline
url https://www.mdpi.com/1420-3049/24/3/463
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AT kunhu efficienttandemadditioncyclizationforaccessto24diarylquinazolinesviacatalyticcarbopalladationofnitriles
AT yetongzhang efficienttandemadditioncyclizationforaccessto24diarylquinazolinesviacatalyticcarbopalladationofnitriles
AT yinlinshao efficienttandemadditioncyclizationforaccessto24diarylquinazolinesviacatalyticcarbopalladationofnitriles
AT tianxingcheng efficienttandemadditioncyclizationforaccessto24diarylquinazolinesviacatalyticcarbopalladationofnitriles
AT maolinhu efficienttandemadditioncyclizationforaccessto24diarylquinazolinesviacatalyticcarbopalladationofnitriles
AT jiuxichen efficienttandemadditioncyclizationforaccessto24diarylquinazolinesviacatalyticcarbopalladationofnitriles