Jump to main content
Jump to site search


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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 Nov 2018, accepted on 05 Dec 2018 and first published on 05 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02857E
Citation: Org. Biomol. Chem., 2019, Advance Article
  •   Request permissions

    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, Advance Article , DOI: 10.1039/C8OB02857E

Search articles by author

Spotlight

Advertisements