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Issue 24, 2017
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I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

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Abstract

An I2-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving the C[triple bond, length as m-dash]N cleavage of isocyanides. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

Graphical abstract: I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

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Publication details

The article was received on 28 Dec 2016, accepted on 28 Feb 2017, published on 28 Feb 2017 and first published online on 28 Feb 2017


Article type: Communication
DOI: 10.1039/C6CC10275A
Citation: Chem. Commun., 2017,53, 3438-3441
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    I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

    X. Wu, X. Geng, P. Zhao, J. Zhang, Y. Wu and A. Wu, Chem. Commun., 2017, 53, 3438
    DOI: 10.1039/C6CC10275A

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