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Issue 90, 2017
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A serendipitous cascade of rhodium vinylcarbenoids with aminochalcones for the synthesis of functionalized quinolines

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Abstract

A serendipitous five-step cascade of rhodium vinylcarbenoids with aminochalcones enables a unique synthetic approach to highly functionalized tri- and tetra-cyclic quinolines. The cascade reaction begins with the insertion of aminochalcone nitrogen into rhodium vinylcarbenoids followed by intramolecular aldol cyclization to provide a substituted indoline intermediate that undergoes an oxy-Cope rearrangement to provide a 9-membered azacycle, which then rearranges to the functionalized quinoline through an intramolecular aldol/dehydration sequence. With a catalyst loading as low as 0.1 mol%, the cascade reaction has proven to be general with a range of aminochalcones and vinylcarbenoids.

Graphical abstract: A serendipitous cascade of rhodium vinylcarbenoids with aminochalcones for the synthesis of functionalized quinolines

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Submitted
13 Sep 2017
Accepted
18 Oct 2017
First published
19 Oct 2017

Chem. Commun., 2017,53, 12205-12208
Article type
Communication

A serendipitous cascade of rhodium vinylcarbenoids with aminochalcones for the synthesis of functionalized quinolines

K. Chinthapally, N. P. Massaro, H. L. Padgett and I. Sharma, Chem. Commun., 2017, 53, 12205
DOI: 10.1039/C7CC07181G

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