Preparation of New Nitrogen-Bridged Heterocycles. 46. Selective Formation of 4(1H)-8,8a-Dihydro-1,4-thiazino[3,4,5-cd]indolizinone and (E)-3-(1,3-Oxathiol-2-ylidene)-2(3H)-indolizinone Derivatives

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概要

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• The reactions of (Z)-3-[mercapto(methylthio)methylene]-2(3H)-indolizinones with bromoacetonitrile and bromoacetates in the presence of a base gave the corresponding 4(1H)-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizinone derivatives, but similar treatment of the same compounds with some phenacyl bromides provided a quite different type of product, (E)-3-(5-aryl-1,3-oxathiol-2-ylidene)-2(3H)-indolizinones, in 12-74% yield with the evolution of methanethiol. Interestingly, the reactions of (Z)-3-[mercapto(phenacylthio)methylene]-2(3H)-indolizinones and iodomethane in the presence of a base did not afford the expected (Z)-3-(5-aryl-1,3-oxathiol-2-ylidene)-2(3H)-indolizinones, but gave only the same (E)-isomers in 22-53% yields. The stereochemistry about the C3-C2' double bond in these 3-(5-aryl-1,3-oxathiol-2-ylidene)-2(3H)-indolizinones was determined to be (E) by X-ray analysis.

• 公益社団法人日本薬学会の論文
• 1998-12-15

著者

• Suga Hiroyuki

  Department Of Cardiovascular Dynamics National Cardiovascular Center Research Institute

• Akikazu Kakehi

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Kobayashi T

  Faculty Of Science Shinshu University

• Kakehi Akikazu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Suga Hiroyuki

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Kobayashi Toshiyuki

  Department of Pediatrics, Sapporo Medical University School of Medicine

• Kakehi A

  Dep. Of Chemistry And Material Engineering Fac. Of Engineering Shinshu Univ. Wakasato Nagano 380-855

• Kawanishi T

  大妻女子大学 食物学科

• ITO Suketaka

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• HATANAKA Susumu

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• Suga H

  Dep. Of Chemistry And Material Engineering Fac. Of Engineering Shinshu Univ. Wakasato Nagano 380-855

• Kobayashi Toshiyuki

  Department Of Pediatrics Urakawa Redcross Hospital

• Ito Suketaka

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Kobayashi Toshiyuki

  Department Of Pathology And Oncology Juntendo University School Of Medicine

• Hatanaka Susumu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• KOBAYASHI Toshiyuki

  Department of Experimental Pathology, Cancer Institute, Japanese Foundation for Cancer Research

• SUGA Hiroyuki

  Department of Cardiac Physiology, National Cardiovascular Center Research Institute

• Ito Suketaka

  Department of Applied Chemistry Faculty of Engineering Nagoya University

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