Bulletin of the Chemical Society of Japan p. 68 - 73 (1991)
Update date:2022-09-26
Topics: Organic chemistry Chemical Reaction Related compounds Selective Formation Sulfur Nitride Benzoand Benzobis<1,2,5>thiadiazole Skeleton Tetrasulfur Tetranitride Naphthalenols
Mataka, Shuntaro
Takahashi, Kazufumi
Ikezaki, Youji
Hatta, Taizo
Tori-i, Akiyoshi
Tashiro, Masashi
Tetrasulfur tetranitride (N4S4) reacted with 2-naphthols to afford naphtho<1,2-c><1,2,5>thiadiazoles (13) in high yields, while 1-naphthols gave naphthol<1,2-c:3,4-c'>bis<1,2,5>thiadiazoles as a major product, together with a small amount of 13.In the reactions with naphthalenediols such as 1,5-, 2,6-, 2,7-, 1,6-, and 1,7-diol, naphtho<1,2-c:5,6-c'>- or naphtho<1,2-c:7,8-c'>bis<1,2,5>thiadiazoles were obtained in varying yields.In some cases, naphtho<1,2-c:3,4-c':5,6-c''>tris<1,2,5>thiadiazole was formed as a by-product.In reaction with 5-isoquinolinol, 8-quinolinoles,9H-carbazol-2-ol, and dibenzofuran-2-ol, one and/or two 1,2,5-thiadiazole-ringfused heteroaromatic compounds were obtained.
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