- 著者
- 沢田 誠吾 宮坂 貞 荒川 基一
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.26, no.1, pp.275-287, 1978-01-25 (Released:2008-03-31)
- 被引用文献数
- 2 2
1-(Substituted-phenyl)-2, 3-tetramethylenepyrrolo [2, 1-b] benzothiazoles (IV-2-IV-17) were synthesized from the correspoding 3-(substituted-phenyl) thiazolo [2, 3-b] benzothiazolium perchlorates (III) by the reaction of 1-morpholino-1-cyclohexene, an enamine. On reaction with cuprous cyanide p-substituted bromobenzene (IV-2) furnished benzonitrile (IV-23), which was converted into the corresponding 1-phenyl derivatives (IV) with various aliphatic functional groups at the para position of the phenyl moiety. On reaction with methylmagnesium iodide and subsequent acid hydrolysis IV-23 was converted into acetophenone (IV-24), which reacted with methyltriphenylphosphylene to give 2-phenylpropylene (IV-38). Hydroboration of IV-38 afforded 2-phenylpropanol (IV-39), which was oxidized into the corresponding propionic acid (IV-43), the sulfur atom being oxidized at the same time into sulfoxide. Deoxygenation of the ester (IV-44) was successfully carried out with PBr3 to obtain the desired α-phenyl substituted propionic acid ester (IV-45).
- 著者
- 沢田 誠吾 宮坂 貞 荒川 基一
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.25, no.12, pp.3370-3375, 1977-12-25 (Released:2008-03-31)
- 被引用文献数
- 5 5
Seventeen 3-(substituted-phenyl) thiazolo [2, 3-b] benzothiazolium perchlorates (3) were synthesized by acid-cyclization of the ketosulfides (2), which were prepared by alkylation of 2-mercaptobenzothiazole sodium salt with substituted phenacyl halides (1). Some of the phenacyl halides were prepared by chloroacetylation of substituted benzenes, and the others by bromination of the corresponding substituted acetophenones.