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A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds

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Abstract

A novel and efficient multicomponent reaction for the synthesis of polysubstituted pyrrolidine derivatives is described under catalyst-free conditions using ultrasonic irradiation. The reactions were performed via a one-pot four-component condensation of secondary amines, carbon disulfide, isocyanides, and gem-dicyano olefins at room temperature to afford polysubstituted pyrrolidines diastereoselectively in 56–96% yields. This is the first report of a Mumm-type rearrangement with dithiocarbamates followed by intramolecular cyclization, which leads to the preparation of the key structure of pyrrolidine.

Graphical abstract: A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds

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Article information


Submitted
09 Feb 2020
Accepted
17 May 2020
First published
18 May 2020

New J. Chem., 2020, Advance Article
Article type
Paper

A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds

F. M. Moghaddam, M. Goudarzi, F. Chamani and H. M. Dezag, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ00691B

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