Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids

A simple metal and additive-free approach for the assembly of 5-trifluoromethyl-1,2,4-triazoles via only heating-induced decarboxylative cyclization of readily available trifluoroacetimidohydrazides and α-oxocarboxylic acids has been developed. In this protocol, the rarely reported tetrahedral carbo...

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Main Authors: Yu Zhang, Guangming Wei, Shiqi Qiu, Zhengkai Chen, Xiao Feng Wu
Format: Article
Language:English
Published: KeAi Communications Co. Ltd. 2023-05-01
Series:Green Synthesis and Catalysis
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2666554922000801
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author Yu Zhang
Guangming Wei
Shiqi Qiu
Zhengkai Chen
Xiao Feng Wu
author_facet Yu Zhang
Guangming Wei
Shiqi Qiu
Zhengkai Chen
Xiao Feng Wu
author_sort Yu Zhang
collection DOAJ
description A simple metal and additive-free approach for the assembly of 5-trifluoromethyl-1,2,4-triazoles via only heating-induced decarboxylative cyclization of readily available trifluoroacetimidohydrazides and α-oxocarboxylic acids has been developed. In this protocol, the rarely reported tetrahedral carboxylic acids intermediate could be in-situ generated and undergo subsequent decarboxylation to afford the target heterocycle products.
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spelling doaj.art-34c6a458959a48f184b51cdcc09d6cce2023-06-07T04:49:55ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-05-0142177180Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acidsYu Zhang0Guangming Wei1Shiqi Qiu2Zhengkai Chen3Xiao Feng Wu4Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China; Corresponding author. Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, ChinaDalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China; Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straβe 29a, Rostock 18059, Germany; Corresponding author. Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, ChinaA simple metal and additive-free approach for the assembly of 5-trifluoromethyl-1,2,4-triazoles via only heating-induced decarboxylative cyclization of readily available trifluoroacetimidohydrazides and α-oxocarboxylic acids has been developed. In this protocol, the rarely reported tetrahedral carboxylic acids intermediate could be in-situ generated and undergo subsequent decarboxylation to afford the target heterocycle products.http://www.sciencedirect.com/science/article/pii/S2666554922000801Heating-inducedDecarboxylative cyclization5-Trifluoromethyl-1,2,4-triazolesTrifluoroacetimidohydrazidesα-Oxocarboxylic acidsTrifluoromethyl-substituted N-heterocycles
spellingShingle Yu Zhang
Guangming Wei
Shiqi Qiu
Zhengkai Chen
Xiao Feng Wu
Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids
Green Synthesis and Catalysis
Heating-induced
Decarboxylative cyclization
5-Trifluoromethyl-1,2,4-triazoles
Trifluoroacetimidohydrazides
α-Oxocarboxylic acids
Trifluoromethyl-substituted N-heterocycles
title Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids
title_full Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids
title_fullStr Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids
title_full_unstemmed Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids
title_short Heating-induced decarboxylative cyclization for the synthesis of 5-trifluoromethyl-1,2,4-triazoles from trifluoroacetimidohydrazides and α-oxocarboxylic acids
title_sort heating induced decarboxylative cyclization for the synthesis of 5 trifluoromethyl 1 2 4 triazoles from trifluoroacetimidohydrazides and α oxocarboxylic acids
topic Heating-induced
Decarboxylative cyclization
5-Trifluoromethyl-1,2,4-triazoles
Trifluoroacetimidohydrazides
α-Oxocarboxylic acids
Trifluoromethyl-substituted N-heterocycles
url http://www.sciencedirect.com/science/article/pii/S2666554922000801
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