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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
Further Information

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.

Key words

dipolar cycloadditions - benzothiophenes - polycycles - heterocycles - azomethine ylides

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561428.
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  • References

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