高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

5-(1-芳基-1-吡咯-2-基)-1氢-四唑类化合物的合成与表征

刘伟1, 麻远1, 尹应武2, 赵玉芬1   

    1. 清华大学化学系, 生命有机磷化学及化学生物学教育部重点实验室,
    2. 清华紫光英力化工有限责任公司, 北京 100084
  • 收稿日期:2005-08-18 修回日期:1900-01-01 出版日期:2006-08-10 发布日期:2006-08-10
  • 通讯作者: 赵玉芬

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

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被引次数

4

摘要： 利用阳极氧化反应, 将一系列N-芳基吡咯电氰化, 区域专一地得到吡咯氰化物2, 分离收率为76%~85%. 将其与叠氮化钠反应, 合成了一系列具有潜在血管紧张素Ⅱ受体(AT)拮抗活性的新型四唑化合物. 该合成路线的原料易得, 并以阳极氰化芳香氮杂环引入氰基为关键步骤, 可作为在芳香氮杂环上引入四唑基团的通用合成路线.

关键词: 阳极氰化, 腈, 吡咯, 四唑, 循环伏安法

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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