Studies on Organosulfur Compounds. XI. Selective Cyclization to Benzothiazole by the Reaction between Quinaldine and meta-Substituted Anilines (or Nitro Compounds) under the Modified Willgerodt-Kindler Reaction

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概要

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• In order to clarify in more detail the cyclization mechanism of thioanilides to benzothiazoles under the modified Willgerodt-Kindler reaction condition, quinaldine (I) was heated with meta-substituted anilines (II) or meta-substituted nitrobenzenes (III) in the presence of sulfur. Further, in order to examine on solvent effects through these processes, dimethylformamide (DMF) was employed. Although the yields of these reactions were different, the reactions also gave similarly thioanilides and one of the two possible benzothiazoles. The latter was proved to have the structure of 5-substituted 2-(2-quinolyl) benzothiazoles (V) by independent synthesis. On the other hand, the expected two isomeric benzothiazoles (V and VI) were obtained from the oxidaitve cyclization of thioanilides (IV) by the modified Jacobson reaction. Moreover, the thioanilides obtained from I or 2-picoline were found to react with the corresponding II in the presence of sulfur in DMF at 160-170°to give the selective cyclization product, respectively.

• 社団法人日本薬学会の論文
• 1974-09-25

著者

• 市川 正孝

  福山大学薬学部

• 市川 正孝

  Faculty Of Pharmaceutical Sciences Kumamoto Univerisity

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 久野 拓三

  熊本大学薬学部

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