Sulfur Nitride in Organic Chemistry. Part 19. Selective Formation of Benzo- and Benzobisthiadiazole Skeleton in the Reaction of Tetrasulfur Tetranitride with Naphthalenols and Related Compounds

Article abstract of DOI:10.1246/bcsj.64.68

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.