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A modified synthesis of 4‐chloromethylthiazoles

 

作者: Gifford Marzoni,  

 

期刊: Journal of Heterocyclic Chemistry  (WILEY Available online 1986)
卷期: Volume 23, issue 2  

页码: 577-580

 

ISSN:0022-152X

 

年代: 1986

 

DOI:10.1002/jhet.5570230253

 

出版商: Wiley‐Blackwell

 

数据来源: WILEY

 

摘要:

AbstractA two‐reaction synthesis of 2‐substituted‐4‐chloromethylthiazoles from thioamides and 1,3‐dichloroacetone is reported. The first step, cyclization to a 2‐substituted‐4‐chloromethyl‐4‐hydroxythiazoline is carried out in the presence of bicarbonate in an aprotic solvent. Dehydration of this intermediate to a 2‐substituted‐4‐chloromethylthiazole is accomplished by reaction with thionyl chloride, sulfuryl chloride, phosphoryl chloride, phosphorus trichloride or phosphorus pentachloride. Substituents on the thioamide, such as amino, alkyl, or aryl, are shown not to affect the success of the reaction. As a trend, alkylthioamides give slightly better yields of 4‐chloromethylthiazoles than do arylthioamides. The yields of 4‐chloromethylthiazoles prepared using this procedure are comparable to the yields obtained us

 

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