Abstract
A novel, one-pot synthesis of 3-dimethylamino-4, 1, 2-benzoxathiazine 1, 1-dioxides (7), 3-methoxy-4-methyl-1, 2, 4-benzothiadiazine 1, 1-dioxide (9) and 3-dimethylamino-1, 4, 2-benzodithiazine 1, 1-dioxides (11) is described. The procedure in the case of 7 involves [2+2] cycloaddition reaction of chlorosulfonyl isocyanate (CSI) with thiocarbamates with subsequent loss of carbonyl sulfide, followed by cyclization of the resulting N-chlorosulfonyl isothioureas under Friedel-Crafts conditions. Synthesis of 9 was achieved similarly. Also, by using dithiocarbamates instead of thiocarbamates, the 1, 4, 2-benzodithiazines 11 were synthesized.
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