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Molecules 2016, 21(2), 187; doi:10.3390/molecules21020187

1,3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation

Department of Chemistry, Masaryk University, Kotlářská 2, Brno 611-37, Czech Republic
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Academic Editor: Mark Rizzacasa
Received: 3 December 2015 / Revised: 22 January 2016 / Accepted: 29 January 2016 / Published: 4 February 2016
(This article belongs to the Special Issue Pericyclic Reactions)
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Abstract

This paper describes the synthesis of precursors with a benzo[b]furan skeleton for the intramolecular 1,3-dipolar cycloaddition of azomethine ylides prepared from N-substituted 3-allyl-aminobenzo[b]furan-2-aldehydes and secondary amines derived from α-amino acid esters. Reactions were initiated by heating. The products consisted of four fused rings with three stereogenic centers. Their structure and stereochemistry were determined by NMR spectra and X-ray measurements. View Full-Text
Keywords: 1,3-dipolar cycloaddition; fused heterocycles; thermal initiation; 3-amino-benzo[b]furan-2-carbaldehyde 1,3-dipolar cycloaddition; fused heterocycles; thermal initiation; 3-amino-benzo[b]furan-2-carbaldehyde
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Porubský, M.; Tenora, L.; Potáček, M. 1,3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation. Molecules 2016, 21, 187.

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