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Synthesis 2016; 48(21): 3803-3811
DOI: 10.1055/s-0035-1561653
DOI: 10.1055/s-0035-1561653
paper
Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides
Further Information
Publication History
Received: 17 February 2016
Accepted after revision: 28 April 2016
Publication Date:
20 June 2016 (online)
Abstract
In this study, a one-pot, three-component reaction of two molecules of indane-1,3-dione with aromatic aldehydes for the synthesis of spirocyclopropylindanediones using poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) (PBBS), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide (TBBDA), poly(N-chloro-N-ethylbenzene-1,3-disulfonamide) (PCBS), and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide (TCBDA) as novel reagents has been developed. In addition, an effective and simple domino procedure for the preparation of spirodicyanocyclopropylindanediones from indane-1,3-dione and 2-arylidenemalononitriles is reported. These reactions involve Michael addition, halogenation, and intramolecular ring-closing (MHIRC) reaction sequences.
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