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Synthesis 2014; 46(08): 1059-1066
DOI: 10.1055/s-0033-1340815
DOI: 10.1055/s-0033-1340815
paper
Facile Synthesis of Spiro[indane-2,1′-pyrrolo[2,1-a]isoquinolines] via Three-Component Reaction of Isoquinolinium Salts, Indane-1,3-dione, and Isatins
Further Information
Publication History
Received: 24 December 2013
Accepted after revision: 22 January 2014
Publication Date:
10 February 2014 (online)
Abstract
A series of novel 2′-aryl-2′-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2′,3′-dihydro-10b′H-spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline]-1,3-diones were efficiently synthesized by three-component reactions of in situ generated N-phenacylisoquinolinium bromides with indane-1,3-dione and isatins in ethanol with triethylamine as the base. A domino reaction mechanism for the formation of the spiro compounds was rationally proposed.
Key words
spiro compound - isoquinoline - isatin - indane-1,3-dione - nitrogen ylide - 1,3-cycloadditionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information