Sulfur nitride in organic chemistry. Part 19.1) selective formation of benzo- and benzobis[l,2,5]thiadiazole skeleton in the reaction of tetrasulfur tetranitride with naphthalenols and related compounds

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[l,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-ringfused heteroaromatic compounds were obtained.