Sulfur nitride in organic chemistry. Part 19. Selective formation of benzo- and benzobis(1,2,5)thiadiazole skeleton in the reaction of tetrasulfur tetranitride with naphthalenols and related compounds.

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概要

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• Tetrasulfur tetranitride (N<SUB>4</SUB>S<SUB>4</SUB>) reacted with 2-naphthols to afford naphtho [1,2-<I>c</I>][1,2,5] thiadiazoles (<B>13</B>) in high yields, while 1-naphthaols gave naphtho[1,2-<I>c</I>:3,4-<I>c</I>′]bis[1,2,5]thiadiazoles as a major product, together with a small amount of <B>13</B>. In the reactions with naphthalenediols such as 1,5-, 2,6-, 2,7-, 1,6-, and 1,7-diol, naphtho[1,2-<I>c</I>:5,6-<I>c</I>′]- or naphtho[1,2-<I>c</I>:7,8-<I>c</I>′]bis[1,2,5]thiadiazoles were obtained in varying yields. In some cases, naphtho[1,2-<I>c</I>:3,4-<I>c</I>′:5,6-<I>c</I>″]tris[1,2,5]thiadiazole was formed as a by-product. In reactions with 5-isoquinolinol, 8-quinolinoles, 9<I>H</I>-carbazol-2-ol, and dibenzofuran-2-ol, one and/or two 1,2,5-thiadiazole-ring-fused heteroaromatic compounds were obtained.

• 公益社団法人 日本化学会の論文

著者

• Mataka Shuntaro

  Institute For Materials Chemistry And Engineering (imce) Kyushu University

• Tori-i Akiyoshi

  Kurume National College of Technology

• Hatta Taizo

  Department Of Molecular Science And Technology Graduate School Of Engineering Sciences Kyushu Univer

• Tashiro Masashi

  Department of Molecular Science and Technology, Graduate School of Engineering Sciences, Kyushu University

• Takahashi Kazufumi

  Kurume College of Technology

• Ikezaki Youji

  Department of Molecular Science and Technology, Graduate School of Engineering Sciences, 39, Kyushu University

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