Synthesis 2016; 48(15): 2429-2437
DOI: 10.1055/s-0035-1561428
paper
© Georg Thieme Verlag Stuttgart · New York

The Synthesis of Two Regioisomeric Aldehydes with a Tetrahydrobenzo[b]thiophene Scaffold and Their Application in Solvent-Free Intramolecular 1,3-Dipolar Cycloaddition Reactions

L. Tenora
a   Department of Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic   Email: potacek@chemi.muni.cz
,
S. Man
a   Department of Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic   Email: potacek@chemi.muni.cz
,
E. Van Den Berge
b   Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place Louis Pasteur 1, box L4.01.02, 1348 Louvain-la-Neuve, Belgium
,
M. Potáček*
a   Department of Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic   Email: potacek@chemi.muni.cz
› Author Affiliations
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Publication History

Received: 12 February 2016

Accepted after revision: 07 March 2016

Publication Date:
26 April 2016 (online)


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Abstract

The paper describes the synthesis of two regioisomeric 2-amino-3-formyl- and 3-amino-2-formyl-substituted derivatives of tetrahydrobenzo[b]thiophene and their subsequent thermally initiated reactions with secondary amines to give azomethine ylides that undergo intramolecular 1,3-dipolar cycloadditions. In this way, two series of new fused heterocyclic compounds with three stereogenic centers were prepared. The compounds were identified and their structures were determined.

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