IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives

Oxidative cyclization of 6-chloro-4-pyrimidinylhydrazones 4 with iodobenzene diacetate (IBD) in dichloromethane gives rise to [1,2,4]triazolo[4,3-c]pyrimidine derivatives 5a–o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1,2,4]triazolo[1,5-c]pyrimidines 6...

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Detalles Bibliográficos
Autores principales: Tang, Caifei, Li, Zhiming, Wang, Quanrui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869367/
https://www.ncbi.nlm.nih.gov/pubmed/24367427
http://dx.doi.org/10.3762/bjoc.9.298
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author Tang, Caifei
Li, Zhiming
Wang, Quanrui
author_facet Tang, Caifei
Li, Zhiming
Wang, Quanrui
author_sort Tang, Caifei
collection PubMed
description Oxidative cyclization of 6-chloro-4-pyrimidinylhydrazones 4 with iodobenzene diacetate (IBD) in dichloromethane gives rise to [1,2,4]triazolo[4,3-c]pyrimidine derivatives 5a–o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1,2,4]triazolo[1,5-c]pyrimidines 6a–o in moderate to high yields.
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spelling pubmed-38693672013-12-23 IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives Tang, Caifei Li, Zhiming Wang, Quanrui Beilstein J Org Chem Full Research Paper Oxidative cyclization of 6-chloro-4-pyrimidinylhydrazones 4 with iodobenzene diacetate (IBD) in dichloromethane gives rise to [1,2,4]triazolo[4,3-c]pyrimidine derivatives 5a–o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1,2,4]triazolo[1,5-c]pyrimidines 6a–o in moderate to high yields. Beilstein-Institut 2013-11-25 /pmc/articles/PMC3869367/ /pubmed/24367427 http://dx.doi.org/10.3762/bjoc.9.298 Text en Copyright © 2013, Tang et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tang, Caifei
Li, Zhiming
Wang, Quanrui
IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
title IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
title_full IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
title_fullStr IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
title_full_unstemmed IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
title_short IBD-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent Dimroth rearrangement: Synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
title_sort ibd-mediated oxidative cyclization of pyrimidinylhydrazones and concurrent dimroth rearrangement: synthesis of [1,2,4]triazolo[1,5-c]pyrimidine derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869367/
https://www.ncbi.nlm.nih.gov/pubmed/24367427
http://dx.doi.org/10.3762/bjoc.9.298
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AT lizhiming ibdmediatedoxidativecyclizationofpyrimidinylhydrazonesandconcurrentdimrothrearrangementsynthesisof124triazolo15cpyrimidinederivatives
AT wangquanrui ibdmediatedoxidativecyclizationofpyrimidinylhydrazonesandconcurrentdimrothrearrangementsynthesisof124triazolo15cpyrimidinederivatives

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