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Alkylsulfamoyl Chlorides as Key Units in the Synthesis of Novel Biologically Active Compounds for Crop Protection

 

作者: Gerhard Hamprecht,   Karl‐Heinz König,   Gerd Stubenrauch,  

 

期刊: Angewandte Chemie International Edition in English  (WILEY Available online 1981)
卷期: Volume 20, issue 2  

页码: 151-164

 

ISSN:0570-0833

 

年代: 1981

 

DOI:10.1002/anie.198101511

 

出版商: Hüthig&Wepf Verlag

 

关键词: Alkylsulfamoyl chlorides;Sulfamoyl chlorides;Pesticides;Crop protection

 

数据来源: WILEY

 

摘要:

AbstractDue to their bifunctional character, alkylsulfamoyl chlorides are versatile units for the synthesis of heterocycles, polar sulfamates, and sulfonamides. In the last decade, synthetic methods of general preparative use have been developed, by means of which amine hydrochlorides, isocyanates, aziridines or tertiary alcohols can be reacted with suitable sulfuric acid derivatives to give novel, variously substituted alkylsulfamoyl chlorides. These compounds can subsequently be converted either to previously unobtainableN‐alkoxyalkyl‐N‐alkylsulfamoyl chlorides or to novel heterocycles of the type 1H‐2,1,3‐benzothiadiazin‐4‐one‐2,2‐dioxide, 2H‐1,2,6‐thiadia‐zin‐3‐one‐1,1‐dioxide and 2H‐1,2,4,6‐thiatriazin‐5‐one‐1,1‐dioxide; these compounds are examples of interesting models which illustrate the relation between the structure and the action of the compound, and in some cases lead to highly selective, ecologically unobjectionable herbicides. On the other hand, the alkylsulfamoyl chlorides themselves can beN‐acylated to give further 3‐ to 5‐atom bifunctional synthesis units, with which novel heterocyclic syntheses can be carried out. Further uses of the alkylsulfamoyl chlorides include the preparation of biologically active sulfamates, and cycloaddi

 

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