Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

Beilstein Journal of Organic Chemistry

Yelong Lei¹  Jiaxi Xu¹ 

[1] State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of China;

关键词: aziridine;    diazooxoester;    diazo compound;    ketene;    oxazoline;    ring expansion;   

DOI  :  10.3762/bjoc.18.6

来源: DOAJ

【 摘 要 】

Alkyl 2-diazo-3-oxoalkanoates generate alkoxycarbonylketenes, which undergo an electrophilic ring expansion with aziridines to afford alkyl 2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and catalysts and can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates.

【 授权许可】

Unknown