Synlett 2014; 25(16): 2297-2300
DOI: 10.1055/s-0034-1379107
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© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Tandem Ring-Opening/Click Reaction of Acetylene-Bearing Donor–Acceptor Cyclopropanes

Michelle E. Flisar
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada   Fax: +1(519)6613022   eMail: makerr@uwo.ca
,
Michael R. Emmett
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada   Fax: +1(519)6613022   eMail: makerr@uwo.ca
,
Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada   Fax: +1(519)6613022   eMail: makerr@uwo.ca
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Publikationsverlauf

Received: 18. Juli 2014

Accepted after revision: 21. August 2014

Publikationsdatum:
08. September 2014 (online)


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Abstract

Cyclopropane-1,1-hemimalonates bearing a 2-(2-alkynylphenyl) moiety underwent ring opening by an azide nucleophile, generating an alkyl azide that, in turn, underwent [3+2]-dipolar cycloaddition with the alkyne. The products are novel linearly fused tricyclic 1,2,3-triazoles.

Supporting Information