o-Iodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles

A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles hav...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-04, Vol.77 (8), p.3716-3723
Main Authors: Chaudhari, Pramod S, Pathare, Sagar P, Akamanchi, Krishnacharaya G
Format: Article
Language:English
Subjects:
Azoles - chemical synthesis
Azoles - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Iodobenzenes - chemistry
Models, Chemical
Nitrogen - chemistry
Organic chemistry
Oxidation-Reduction
Preparations and properties
Thiadiazoles - chemical synthesis
Thiadiazoles - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2025509