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Issue 24, 2016
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I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement

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Abstract

A simple and efficient iodine-assisted protocol for the synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones has been developed. The reaction involves a sequential condensation followed by tandem oxidative cyclization and rearrangement of readily available methyl/benzyl carbazates and aldehydes as starting substrates. The presence of iodine and base promotes intramolecular C–O bond formation, followed by Chapman-like rearrangement at 90 °C of the methyl/benzyl group in the hydrazone intermediate formed during the condensation step. This transition-metal-free approach has been adopted to generate a variety of oxadiazolones under mild conditions in good to excellent yields.

Graphical abstract: I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement

  • This article is part of the themed collection: New Talent
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Article information


Submitted
29 Dec 2015
Accepted
02 Feb 2016
First published
02 Feb 2016

Org. Biomol. Chem., 2016,14, 5683-5689
Article type
Paper

I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement

S. S. Patel, N. Chandna, S. Kumar and N. Jain, Org. Biomol. Chem., 2016, 14, 5683
DOI: 10.1039/C5OB02667A

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