期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 2, 页码 438-444出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo302324r
关键词
-
资金
- National Research Foundation of Korea [2010-0004128]
- Ministry of Education, Science and Technology
- Ministry of Knowledge Economy, Korea
- Korea Evaluation Institute of Industrial Technology (KEIT) [M005500004] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- National Research Foundation of Korea [2010-0004128] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
A regioselective, reagent-based method for the cyclization reaction of 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole core skeletons is described. The thiosemicarbazide intermediate 3 was reacted with EDC center dot HCl in DMSO or p-TsCl, triethylamine in N-methyl-2-pyrrolidone to give the corresponding 2-amino-1,3,4-oxadiazoles 4 and 2-amino-1,3,4-thiadiazoles 5 through regioselcective cyclization processes. The regioselectivity was affected by both R-1 and R-2 in p-TsCl mediated cyclization. It is shown in select sets of thiosemicarbazide 3 with R-1(benzyl) and R-2(phenyl). 2-Amino-1,3,4-oxadiazole 4 was also shown in the reaction of p-TsCl mediated cyclization. The resulting 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole core skeleton are functionalized with various electrophiles such as alkyl halide, acid halides, and sulfornyl chloride in high yields.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据