Preparation of New Nitrogen-Bridged Heterocycles. 28. First Syntheses of 1,3-Oxazino(6,5-b)indolizine Derivatives.

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概要

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• The reactions of 2-[mercapto(methylthio)methylene]-2(3<I>H</I>)-indolizinones with alkyl isothiocyanates in the presence of potassium <I>t</I>-butoxide in <I>N</I>,<I>N</I>-dimethylformamide afforded new heterocycles, 3-alkyl-2<I>H</I>-1,3-oxazino[6,5-<I>b</I>]indolizine-2,4(3<I>H</I>)-dithione derivatives, in moderate yields. On the other hand, their reactions with phenyl isothiocyanate did not afford the corresponding 2<I>H</I>-1,3-oxazino[6,5-<I>b</I>]indolizine-2,4(3<I>H</I>)-dithiones, although the reaction of 2-[mercapto(methylthio)methylene]-1-methyl-2(3<I>H</I>)-indolizinone with phenyl isothiocyanate gave 10-methyl-3-phenyl-2-phenylimino-2,3-dihydro-4<I>H</I>-1,3-oxazino[6,5-<I>b</I>]indolizine-4-thione in a very low yield (10%). The structures of these 2<I>H</I>-1,3-oxazino[6,5-<I>b</I>]indolizine-2,4(3<I>H</I>)-dithiones and the 2-phenylimino analogue were determined by inspections of their physical and spectral data and by a single crystal X-ray analysis of one of these compounds.

• 公益社団法人 日本化学会の論文

著者

• Kakehi Akikazu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Hatanaka Susumu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Ito Suketaka

  Department of Applied Chemistry Faculty of Engineering Nagoya University

• Sakurai Tosio

  Department of Science, Faculty of Education, Shinsyu University

• Urushido Kunio

  Department of Chemistry, Faculty of Education, Shinshu University

• Sugiura Kouji

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

• Sakurai Tosio

  Department of Chemistry, Faculty of Education, Shinshu University

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