S-Alkylation en s�rie h�t�rocyclique par catalyse par transfert de phase: thioalkyl-2-thiazoles, thioalkyl-2-?-4-thiazolines et thioalkyl-2-benzothiazoles
作者:Henri J. M. Dou、Parina Hassanaly、Jacky Kister、Gaston Vernin、Jacques Metzger
DOI:10.1002/hlca.19780610842
日期:1978.12.13
S-Alkylation in heterocyclic serie by phase transfer catalysis: 2-alkylthiothiazoles, 2-alkylthio-Δ-4-thiazolines and 2-alkylthiobenzothiazoles
相转移催化在杂环系列中的S-烷基化:2-烷硫基噻唑,2-烷硫基-Δ-4-噻唑啉和2-烷硫基苯并噻唑
Studies on 2-Substituted Thiazolines. L. Reaction with Cyanoacetic Acid
2-Substituted thiazokines (IIa-d) were prepared from 2-thiothiazokidone. IIa-d were converted to 2-(ethoxycarbonylcyanomethylene) thiazolidine (III) and its N-acetate and N-methyl derivative. Thiolester analogs of III were obtained by the reaction of IIa-d and cyanoacetic acid in acetic anhydride.
2-Alkylthiothiazokines were reacted with heterocycles such as rhodanines and thiazolidine-2, 4-dione in acetic anhydride to give the condensed products, (Va) and (X). The intermediates, (IIIa), (IVa) and (IX) were also obtained. The structures of these compounds were established by spectral data.
This article reports a mild protocol for visible-light-mediated Minisci-type C−H alkylation reactions of N-heteroarenes with 2-mercaptothiazolinium salts without using extra acids, furnishing the corresponding functionalized N-heteroarenes in good to high yields.