1,3-DIPOLAR CYCLOADDITION OF 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLIUM BETAINES

被引：12
|
作者：
KIM, DJ [1 ]
YOO, KH [1 ]
PARK, SW [1 ]
机构：
[1] KOREA ADV INST SCI & TECHNOL,DIV CHEM,SEOUL 131650,SOUTH KOREA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 08期
关键词：
D O I：
10.1021/jo00034a029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
5,6-Dihydroimidazo[2,1-b]thiazolium betaines were generated in situ from 3,7-disubstituted 5,6-dihydroimidazo[2,1-b]thiazolium bromides and triethylamine. The reaction of these imidazothiazolium betaines with acetylenic dipolarophiles, such as ethyl propiolate, dimethyl acetylenedicarboxylate, and dibenzoylacetylene, provided geometric cis,trans isomers containing 2,3-dihydro-1H-pyrrolo[1,2-a]imidazole. We have proposed a mechanism of this reaction that involves 1,3-dipolar cycloaddition, isomeric rearrangement, and then nucleophilic addition successively. The ratio of trans and cis isomers depended on the temperature and solvents. The stereoselectivity of trans isomers increased with increasing temperature and decreasing polarity of solvents.
引用
收藏
页码：2347 / 2352
页数：6
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