Issue 12, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Nitrogen substituted cyclic enediynes: synthesis, thermal reactivity and complexation with metal ions

Amit Basak,*a   Jagadish Chandra Shain,a   Uttam Kumar Khamrai,a   Kakali Rani Rudraa  and  Ajoy Basakb  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology, Kharagpur, India

b Loeb Research Institute, Ottawa Civic Hospital, University of Ottawa, 725 Parkdale Avenue, Ottawa, ON, Canada

Abstract

A number of N-substituted cyclic enediynes (azaenediynes) have been synthesized via Pd(0)-catalysed ene–yne coupling followed by N-alkylation. The simplest of them, a 10-membered monocyclic enediyne 1, underwent Bergman cyclization (BC) at 23 °C with a half-life of 72 h. The kinetics of BC slowed down considerably by fusing a benzene ring onto the enediyne. Several novel bis(azaenediyne)s and bis(diazaenediyne)s 3–6 have been synthesized. Their onset temperatures for BC were lowered under metal ion complexation conditions.

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Article information

DOI
https://doi.org/10.1039/B000963F
Article type
Paper
Submitted
03 Feb 2000
Accepted
05 Apr 2000
First published
31 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1955-1964

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Nitrogen substituted cyclic enediynes: synthesis, thermal reactivity and complexation with metal ions

A. Basak, J. C. Shain, U. K. Khamrai, K. R. Rudra and A. Basak, J. Chem. Soc., Perkin Trans. 1, 2000, 1955 DOI: 10.1039/B000963F

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