电催化合成2,5-二取代1,3,4-噁二唑衍生物

doi:10.6023/cjoc202002029

摘要/Abstract

1，3，4-噁二唑作为一种多杂原子的五元杂环类化合物，不仅具有抗炎、抗肌醇和抗惊厥等生物活性，而且是一种重要的有机合成中间体，对其进行合成研究具有重要意义.利用廉价易得的醛和酰肼作为原料，在电催化条件下，一步合成非对称的2，5-二取代1，3，4-噁二唑衍生物，收率良好.其结构经IR、¹H和¹³C NMR、HRMS等进行了确证.该反应条件温和，原子经济性高，底物范围广，为构建1，3，4-噁二唑骨架提供了一种绿色、可持续的合成途径.

关键词: 绿色化学, 1,3,4-噁二唑衍生物, 电化学合成, 自由基环化

1,3,4-Oxadiazoles, standing for a class of five-membered heterocyclic compounds with multiple heteroatoms, show anti-inflammatory, anti-convulsant, anti-inositol and other biological activities. They also served as important intermediates in organic synthesis. Thus, the development of general and straightforward methods for their synthesis is of great significance. In this paper one-step synthesis of non-symmetric 2,5-disubstituted 1,3,4-oxadiazole derivatives with good yield was completed under electrocatalytic conditions by using cheap and readily available aldehydes and hydrazides as starting materials. Their structures were confirmed by IR, ¹H NMR, ¹³C NMR and HRMS analyses. The reaction features mild conditions, high atom-economy and wide substrate scope, providing a green and sustainable synthetic protocol for constructing 1,3,4-oxadiazole skeleton.

Key words: chemistry, 1,3,4-oxadiazoles, electrosynthesis, radcial cyclization

引用此文

李梦帆, 王榕, 郝文娟, 姜波. 电催化合成2,5-二取代1,3,4-噁二唑衍生物[J]. 有机化学, 2020, 40(6): 1540-1548.

Li Mengfan, Wang Rong, Hao Wenjuan, Jiang Bo. Electrocatalytic Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1540-1548.

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