Synlett 2014; 25(5): 608-614
DOI: 10.1055/s-0033-1340549
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© Georg Thieme Verlag Stuttgart · New York

Employing Arynes in Transition-Metal-Free, N-Heterocycle- Initiated Multicomponent Reactions

Anup Bhunia
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India   Fax: +91(20)25902629   Email: at.biju@ncl.res.in
,
Akkattu T. Biju*
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune 411008, India   Fax: +91(20)25902629   Email: at.biju@ncl.res.in
› Author Affiliations
Further Information

Publication History

Received: 06 November 2013

Accepted after revision: 03 December 2013

Publication Date:
14 January 2014 (eFirst)

Abstract

Transition-metal-free multicomponent reactions involving arynes, N-heterocycles, and various carbonyl compounds have been reported. With (iso)quinoline as the nucleophile and carbonyl compounds, such as aldehydes, ketones, and N-substituted isatins as electrophiles, the reaction afforded oxazino (iso)quinoline derivatives and the reaction proceeded via 1,4-dipolar intermediates. Interestingly, when the nucleophilic trigger used is pyridine, the reaction furnished indolin-2-one derivatives, and it is probable that the reaction proceeds via a pyridylidene intermediate.

 
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