摘要
目的:优化3-芳硫基咪唑并[1,5-a]喹啉化合物的合成工艺。方法:以咪唑并[1,5-a]喹啉和磺酰肼为原料,合成3-芳硫基咪唑并[1,5-a]喹啉类化合物;对原料的投料量、反应促进剂的投料量、反应温度、溶剂用量进行优化研究;并考察底物取代基的变化对反应产率的影响;所有硫醚化产物均通过核磁共振氢谱、碳谱、高分辨质谱来表征结构。结果:以水作为溶剂,一当量的碘作为反应促进剂,咪唑并[1,5-a]喹啉与磺酰肼的投料比为1∶1.5,在密封反应管中,于110℃反应12 h,可以高产率的获得3-芳硫基咪唑并[1,5-a]喹啉类化合物。结论:该合成工艺以水作为溶剂,不使用金属,符合绿色化学要求,适合用于制备3-芳硫基咪唑并[1,5-a]喹啉类化合物。
Objective： To optimize the synthesis process of 3-arylthioimidazo[1,5-a]quinolines. Methods： A route to the synthesis of 3-arylthioimidazo[1,5-a]quinolines has been developed from sulfonyl hydrazines and imidazo[1,5-a]quinolines. The amount of the starting material,the amount of promoter,reaction temperature and solvent dosage were optimized. The effect of substituents on reaction yield were also examined. The structure of the target molecules was characterized by1 H and13C NMR spectroscopy and high resolution mass spectrometry. Results： The optimized reaction conditions involved the use of iodine（ 1 equiv.） as promoter in water at 110℃ in sealed tube for 12 h. The molar ratio of imidazo[1,5-a]quinoline to sulfonyl hydrazine was 1∶ 1. 5. The target molecules（ 3-arylthioimidazo[1,5-a]quinolines） were obtained in excellent yields under the optimized conditions. Conclusion： The synthetic process,which involved the use of water as the solvent under metal free conditions,accords the original idea of the green chemistry and is suitable for preparation of 3-sulfenylated imidazo[1,5-a]quinolines.
作者
冯承涛
魏晗
彭亚
FENG Cheng - Tao WEI Han PENG Ya(School of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, China)
出处
《安徽科技学院学报》
2017年第3期53-57,共5页
Journal of Anhui Science and Technology University
基金
国家自然科学基金(81403114)
安徽高校自然科学研究项目(KJ2017A080)
安徽理工大学青年基金(12797)
关键词
咪唑并[1
5-a]喹啉
硫醚
磺酰肼
碘
Imidazo[1
5-a]quinoline
Thioether
Sulfonyl hydrazine
Iodine
