The (1H-Tetrazol-1-yl)arenediazonium Salts as Convenient Reagents for Quinones Arylation: Synthesis of 1,3-Benzoxathiol-2-ones and Naphtho[2,1-d][1,3]oxathiol-2-ones Bearing (1H-Tetrazol-1-yl)phenyl Motif

A convenient two-step method for the synthesis of novel 1,3-benzoxathiol-2-ones and naphtho[2,1-d][1,3]oxathiol-2-ones bearing (1H-tetrazol-1-yl)phenyl motif was developed. As a key step synthesis, an arylation quinones (1,4-benzoquinone, 1,4-naphtho-quinones) with (1H-tetrazol-1-yl)arenediazonium salts studied efficient protocols were elaborated to obtain variety substituted ((1H-tetrazol-1-yl)phenyl) benzo/naphtho-1,4-quinones in good excellent yields. An alternative naphtho-1,4-quinones via Diels-Alder reaction tetrazolylphenyl-1,4-benzoquinones demonstrated. The prepared readily react thiourea at room temperature presence strong mineral acid form intermediate isothiuronium salts, which cyclize high yields condense 1,3-oxathiol-2-ones under heating.