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Synthesis 2013; 45(4): 545-555
DOI: 10.1055/s-0032-1316839
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquino­lines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation­

Kaushik Brahma
Chemistry Division, Indian Institute of Chemical Biology (CSIR), 4, Raja S. C. Mullick Road, Kolkata 700032, India   Fax: +91(33)24735971   eMail: chinmay@iicb.res.in
,
Basudeb Achari
Chemistry Division, Indian Institute of Chemical Biology (CSIR), 4, Raja S. C. Mullick Road, Kolkata 700032, India   Fax: +91(33)24735971   eMail: chinmay@iicb.res.in
,
Chinmay Chowdhury*
Chemistry Division, Indian Institute of Chemical Biology (CSIR), 4, Raja S. C. Mullick Road, Kolkata 700032, India   Fax: +91(33)24735971   eMail: chinmay@iicb.res.in
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Publikationsverlauf

Received: 05. November 2012

Accepted after revision: 06. Dezember 2012

Publikationsdatum:
04. Januar 2013 (online)

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Abstract

An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types.

Key words

1,2,3-triazoles - nitrogen heterocycles - intramolecular reactions - azide-alkyne cycloaddition - bis-heteroannulations

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are the preparation and characterization data of 7a–d, X-ray crystallographic data of 4a and copies of 1H and 13C NMR spectra of compounds 7a–d, 1–4, 11a–b, 13a–d, 1a′–4a′, 14a.
  • Supporting Information
 

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