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

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 manipulati...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 21; p. 7567
Main Authors Zhang, Shuitao, Li, Jianxin, Xiao, Tiebo, Yang, Baomin, Jiang, Yubo
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 04.11.2022
MDPI
Subjects
Amination
Antibiotics
Carbon
cascade
Chemical bonds
cyclizations
Functional groups
fused 1,2,3-triazoles
isoquinoline
quinazoline
Silver
Substrates
Triazoles
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Summary: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.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27217567