摘要
为了寻找新的含噻唑杂环的先导化合物,利用2-取代-1,3-噻唑烷1与氯甲酸取代苯基酯2及取代苯基甲酰氯4在三乙胺存在下发生缩合反应,合成了6个2-取代-1,3-噻唑烷-3-甲酸酯类化合物3和5个N-苯甲酰基-2-取代-1,3-噻唑烷类化合物5,并利用1HNMR,IR,MS,元素分析对其结构进行了表征.用X-ray单晶衍射测定了2-硫代-1,3-噻唑烷-3-甲酸苯酯(3d)和N-苯甲酰基-2-氧代-1,3-噻唑烷(5a)的晶体结构,证实了氯甲酸酯与2-硫代-1,3-噻唑烷的反应产物为硫酮式结构,而非硫酯式结构.初步生物活性试验结果表明,在试验浓度下部分目标化合物3和5具有一定的杀菌和杀虫活性.
In order to find new thiazole-heterocycle lead compounds, six 2-oxo/thio-1,3-thiazolidine- 3-carboxylates 3 and five N-substituted benzoyl-2-oxo/thio-1,3-thiazolidines 5 were synthesized from a condensation reaction of 2-oxo/thio-1,3-thiazolidine I and substituted phenyl chloroformates 2 or substituted benzoyl chlorides 4 in presence of Et3N. Their structures were confLrmed by 1H NMR, IR, MS spectra and elemental analysis. The crystal structures of phenyl 2-thiono-1,3-thiazolidine-3-carboxylate （3d） and N-benzoyl-2-oxo-1,3-thiazolidine （5a） were determined by X-ray diffraction analysis, and the structure of the condensation products of 2-thiono-1,3-thiazolidine with substituted phenyl chloroformates was proved to be 2-thiono-1,3-thiazolidine-3-carboxylate rather than the ester of mercaptothiazoline. The preliminary bio- assay showed that compounds 3 and 5 exhibited certain fungicidal and insecticidal activities.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2007年第1期126-130,共5页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.30500339)
浙江省教育厅基金(No.20060802)资助项目.
关键词
2-取代-1
3-噻唑烷
氯甲酸取代苯基酯
取代苯基甲酰氯
结构
生物活性
2-oxo/thio-1,3-thiazolidine
substituted phenyl chloroformate
substituted benzoyl chloride
structure
biological activity
