Chem. J. Chinese Universities

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Synthesis of 5-[1-Aryl-pyrrol-2-yl]-1H-tetrazole

LIU Wei1, MA Yuan1, YIN Ying-Wu2, ZHAO Yu-Fen1   

    1. The Key Laboratory for Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University;
    2. Beijing TH-UNIS Insight Co. Ltd., Beijing 100084, China
  • Received:2005-08-18 Revised:1900-01-01 Online:2006-08-10 Published:2006-08-10
  • Contact: ZHAO Yu-Fen1

Abstract: In this paper, tetrazole ring systems were sythesized by using readily available materials via anodic cyanations of suitably N-substituted pyrrole as key step. The electrooxidation of several 1-arylpyrroles was carried out in methanol containing sodium cyanide at a Pt anode in a divided cell. In all instances, replacement of a heteroaromatic hydrogen by a cyano group occurred regio-selectively. The corresponding pyrrole cyanides were obtained in yields ranging from 76% to 85%. The advantages of electrochemistry synthesis of pyrrole cyanides are as follows: the reaction condition is simple, the cost is low and the products is highly pure. The new tetrazole derivatives which may be non-peptidic compounds with potential angiotensin Ⅱ antagonist properties, were synthesized by the formal [2+3] cycloaddition of NaN3 and pyrrole cyanides.

Key words: Anodic cyanation, Nitrile, Pyrrole, Tetrazole, Cyclic voltammetry

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