Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfon­amides

Ramin Ghorbani-Vaghei; Yaser Maghbooli

doi:10.1055/s-0035-1561653

Synthesis, Table of Contents

Synthesis 2016; 48(21): 3803-3811
DOI: 10.1055/s-0035-1561653

paper

Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides

Ramin Ghorbani-Vaghei*

Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran Email: rgvaghei@yahoo.com

,

Yaser Maghbooli

Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran Email: rgvaghei@yahoo.com

› Author Affiliations

Abstract

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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.

Key words

N-halosulfonamides - spirocycles - Michael addition - cyclopropane - indane-1,3-dione - ring closure

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References

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Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfon­amides

Synthesis of Activated Cyclopropanes by MHIRC Strategy: A Facile and Efficient Approach to Spirocyclopropanes Using N-Halosulfonamides