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Issue 2, 2019
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Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives

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Abstract

An unprecedented catalytic isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes was developed for the direct and efficient synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives. On the basis of DFT calculations, a mechanism is proposed involving formal [4 + 1] cycloaddition of isocyanides, followed by imine–enamine tautomerization and air oxidation.

Graphical abstract: Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives

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Article information


Submitted
15 Nov 2018
Accepted
05 Dec 2018
First published
05 Dec 2018

Org. Biomol. Chem., 2019,17, 275-282
Article type
Paper

Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives

M. Motaghi, H. Khosravi, S. Balalaie and F. Rominger, Org. Biomol. Chem., 2019, 17, 275
DOI: 10.1039/C8OB02857E

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