Synthesis 2015; 47(18): 2781-2790
DOI: 10.1055/s-0034-1378717
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Reactivity of Aziridines with Internal Dipolarophiles: An Approach to 1,4-Dihydrochromeno[4,3-b]pyrroles and 3-Methylenechromano[4,3-b]pyrroles

Fernanda M. Ribeiro Laia
Centro de Química de Coimbra, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal   Email: tmelo@ci.uc.pt
,
Teresa M. V. D. Pinho e Melo*
Centro de Química de Coimbra, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal   Email: tmelo@ci.uc.pt
› Author Affiliations
Further Information

Publication History

Received: 09 April 2015

Accepted after revision: 01 May 2015

Publication Date:
24 June 2015 (online)

Abstract

Aziridines derived from 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)chalcones and from benzyl 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)phenylacrylates were prepared in a stereoselective fashion. Their reactivity as azomethine ylide precursors was examined, leading to the synthesis of 1,4-dihydrochromeno[4,3-b]pyrrole and 3-methylenechromano[4,3-b]pyrrole derivatives through intramolecular 1,3-dipolar cycloaddition reactions.

Supporting Information

 
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