二氯二氰基苯醌氧化N-酰基腙制备1,3,4-噁二唑及抗真菌活性研究  

2,3-DICHLORO-5,6-DICYANOBENZOQUINONE PROMOTED OXIDATIVE CYCLIZATION OF N-AROYLHYDRAZONES TO 1,3,4-OXADIAZOLES AND THE PRELIMINARY ANTIFUNGAL ACTIVITY

作　　者：雷英杰[1] 姚庆佳 丁玫[1] 

机构地区：[1]天津理工大学化学化工学院,天津300384 [2]天津市斯芬克司药物研发有限公司,天津300457

出　　处：《精细石油化工》2017年第2期63-67,共5页Speciality Petrochemicals

基　　金：天津市科技特派员项目(16JCTPJC49800)

摘　　要：为了寻找新型的生物活性杂环化合物,改进和优化1,3,4-噁二唑的合成工艺,利用芳酰肼和(取代)苯甲醛为原料,反应生成的N-酰基腙中间体不经过分离,直接在二氯二氰基苯醌的氧化条件下,通过环合反应"一锅法"制备得到1,3,4-噁二唑衍生物,该反应条件温和,合成收率为61%~90%,化合物结构经IR、~1H NMR和元素分析等技术进行了确证;初步的活性测试结果表明,目标产物对尖孢镰刀菌、番茄早疫病菌和白色念珠菌等有较显著的抗菌活性。In order to develop new heterocyclic compounds with biological activity and to optimize the procedure for synthesis of 1,3,4-oxadiazoles,an efficient one-pot protocol via the oxidative cyclization of aldehyde-N-aroylhydrazone,directly from the starting arylhydrazides and aromatic aldehydes catalyzed by 4-methylbenzenesulfonic acid without further treatment,in presence of 2,3-dichloro-5,6-dicyanobenzoquinone（DDQ）to synthesis of 1,3,4-oxadiazoles（3a-3j）has been studied.The results indicated that intramolecular cyclization was performed well with good yields of 61%-90% respectively.The chemical structures of target compounds were confirmed by by IR,~1H NMR spectra and elemental analysis.The investigation on preliminary bioassay showed that some of the target compounds have significant antifungal activity against Fusarium oxysporum,Alternaria solani,and Candida albicans.

关 键 词：N-酰基腙 二氯二氰基苯醌 1 3 4-噁二唑 抗真菌活性 

分 类 号：O626.24[理学—有机化学]