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Issue 44, 2020
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A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones

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Abstract

A three-component reaction between one molecule of phosphorus ylides (P-ylides) and two molecules of isocyanates for the rapid assembly of 2-amino-3-carboxylate-4-quinolones is described. The mechanism may involve the addition of a P-ylide to an isocyanate followed by 1,3-H shift to form a carbamoyl stabilized P-ylide. The intermediate then reacts with another aryl isocyanate via Wittig/ketenimine-ketene rearrangement/6π-electrocyclization/1,3-H shift to finally afford the 4-quinolones.

Graphical abstract: A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones

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Article information


Submitted
22 Feb 2020
Accepted
17 Apr 2020
First published
17 Apr 2020

Chem. Commun., 2020,56, 5909-5912
Article type
Communication

A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones

K. R. Babu, W. Han, J. Chen, Y. Li, Y. Tang, W. Zhang, W. Xu and S. Xu, Chem. Commun., 2020, 56, 5909
DOI: 10.1039/D0CC01401J

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