Milad Motaghi, Hormoz Khosravi, Saeed Balalaie and Frank Rominger
Org. Biomol. Chem., 2019,17, 275-282
DOI:
10.1039/C8OB02857E,
Paper
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](/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=C8OB02857E "Graphical abstract")
