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

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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Bibliographic Details
Main Authors: Caifei Tang, Zhiming Li, Quanrui Wang
Format: Article
Language:English
Published: Beilstein-Institut 2013-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
cyclization
hydrazones
hypervalent iodine
oxidation
rearrangement
[1,2,4]triazolo[1,5-c]pyrimidines
Online Access:https://doi.org/10.3762/bjoc.9.298
Description
Summary: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.
ISSN:1860-5397

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