水介质中1H-吡唑并[3,4-d]嘧啶-4(5H)-酮的快捷高效合成
收稿日期: 2021-04-19
修回日期: 2021-05-10
网络出版日期: 2021-06-08
基金资助
中国医学科学院医学与健康科技创新工程(2018-I2M-1-004); 中央级公益性科研院所基本科研业务费专项(2021GJZ05)
An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water
Received date: 2021-04-19
Revised date: 2021-05-10
Online published: 2021-06-08
Supported by
Chinese Academy of Medical Sciences Innovation Fund for Medical Sciences(2018-I2M-1-004); Non-profit Central Research Institute Fund of National Research Institute for Family Planing(2021GJZ05)
吡唑并嘧啶酮类化合物由于其与生物体内嘌呤的结构相似而具有多种活性, 进而被广泛研究和应用. 吡唑并嘧啶酮类化合物传统的合成方法存在一些不足, 如需要酰化、环化两步完成等. 报道了一种以水为介质、氢氧化钠作用下的5-氨基-4-氰基吡唑和芳香醛一锅环合形成1H-吡唑并[3,4-d]嘧啶-4(5H)-酮的方法. 该方法具有原料易得、操作简单、良好的底物耐受性等优点.
关键词： 一锅转化; 吡唑并[3,4-d]嘧啶-4(5H)-酮; 氢氧化钠; 绿色溶剂; 水
苏子琦 , 张奇 , 赵界强 , 赵涛 , 刘文艺 , 王慧萍 , 徐娟 , 李加荣 . 水介质中1H-吡唑并[3,4-d]嘧啶-4(5H)-酮的快捷高效合成[J]. 有机化学, 2021 , 41(9) : 3701 -3709 . DOI: 10.6023/cjoc202104043
Abstract Pyrazolopyrimidinone compounds have many biological activities and been widely used due to the similar structure of purines in organisms. However, the traditional synthetic methods suffered from several drawbacks, such as acylation and cyclization. Herein, one pot cyclization of 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one was developed by one pot conversion of 5-amino-4-cyano-pyrazole and aromatic aldehydes in the presence of sodium hydroxide using water as media. The reaction was carried out under the conditions of easily available raw materials, simple operation, and showed good tolerance to various functional groups.
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