Studies of Heterocyclic Compounds. XVIII. Synthesis of 1-(Substitutedphenyl)-2,3-tetramethylenepyrrolo [2,1-b] benzothiazoles

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概要

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• 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 PBr_3 to obtain the desired α-phenyl substituted propionic acid ester (IV-45).

• 公益社団法人日本薬学会の論文
• 1978-01-25

著者

• 宮坂 貞

  School of Pharmaceutical Sciences, Showa University

• 澤田 誠吾

  Yakult Central Institute of Microbiological Research

• 澤田 誠吾

  ヤクルト本社中央研究所

• Sawada S

  Yakult Central Institute Of Microbiological Research

• 宮坂 貞

  School Of Pharmaceutical Sciences Showa University

• 沢田 誠吾

  School of Pharmaceutical Sciences, Showa University

• 荒川 基一

  School of Pharmaceutical Sciences, Showa University

• 荒川 基一

  School Of Pharmaceutical Sciences Showa University

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