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

Abstract

Abstract Tetrasulfur tetranitride (N4S4) reacted with 2-naphthols to afford naphtho [1,2-c][1,2,5] thiadiazoles (13) in high yields, while 1-naphthaols gave naphtho[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 reactions with 5-isoquinolinol, 8-quinolinoles, 9H-carbazol-2-ol, and dibenzofuran-2-ol, one and/or two 1,2,5-thiadiazole-ring-fused heteroaromatic compounds were obtained.