A new multicomponent reaction: unexpected formation of derivatizable cyclic α-alkoxy isothioureas

被引：8

作者：

Brockmeyer, Fabian ^{[1
]}

Morosow, Valentin ^{[1
]}

Martens, Juergen ^{[1
]}

机构：

[1] Carl von Ossietzky Univ Oldenburg, Inst Chem, D-26111 Oldenburg, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 11期

关键词：

ROUTE;

D O I：

10.1039/c4ob02608j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected formation of cyclic alpha-alkoxy isothioureas has been achieved. As is known, the heterocyclic imines 2,5-dihydro-1,3-thiazoles are convertible to bisamides with the aid of a carboxylic acid and an isocyanide (Ugi reaction). Herein, it is shown that 2,5-dihydro-1,3-thiazole S-monoxides-the respective alpha-sulfinyl imines-are characterized by an altered reaction behavior. In a hitherto unknown multicomponent reaction the alpha-sulfinyl imines react with an isocyanide under acidic conditions in an alcoholic solution to the respective alpha-alkoxy isothioureas in good yields. In addition to the investigations on this unexpected synthesis the regioselectivity of the acylation of the synthesized compounds is described. A rearrangement, which is accelerated by EDC and HOBt, between both possible regioisomers was found.

引用

页码：3341 / 3346

页数：6

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