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Silver-Catalyzed Cascade Cyclization of Amino-NH-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles.

ABSTRACT: An operationally simple Ag(I)-catalyzed approach for the synthesis of isoquinoline and quinazoline fused 1,2,3-triazoles was developed by a condensation and amination cyclization cascade of amino-NH-1,2,3-triazoles with 2-alkynylbenzaldehydes involving three new C-N bond formations in one manipulation, in which the group of -NH of the triazole ring serves as a nucleophile to form the quinazoline skeleton. The efficient protocol can be applied to a variety of substrates containing a range of functional groups, delivering novel pentacyclic fused 1,2,3-triazoles in good-to-excellent yields.

SUBMITTER: Zhang S 

PROVIDER: S-EPMC9655256 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Silver-Catalyzed Cascade Cyclization of Amino-<i>NH</i>-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles.

Zhang Shuitao S   Li Jianxin J   Xiao Tiebo T   Yang Baomin B   Jiang Yubo Y  

Molecules (Basel, Switzerland) 20221104 21

An operationally simple Ag(I)-catalyzed approach for the synthesis of isoquinoline and quinazoline fused 1,2,3-triazoles was developed by a condensation and amination cyclization cascade of amino-<i>NH</i>-1,2,3-triazoles with 2-alkynylbenzaldehydes involving three new <i>C</i>-<i>N</i> bond formations in one manipulation, in which the group of -<i>NH</i> of the triazole ring serves as a nucleophile to form the quinazoline skeleton. The efficient protocol can be applied to a variety of substrate  ...[more]

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