2H-1,3,2-dioxaborino-[5,4-c]-1,2-benzo-thiazine 6,6-dioxides

Details 2H-1,3,2-dioxaborino-[5,4-c]-1,2-benzo-thiazine 6,6-dioxides 2H-1,3,2-dioxaborino-[5,4-c]-1,2-benzo-thiazine 6,6-dioxides

1975-03-17

1976-06-29

Ford, John M.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424249, C07D27902

Patent

active

039667162

ABSTRACT:
Process for the production of substituted pyrano[3,2-c] [1,2]benzothiazine 6,6-dioxides and novel intermediates produced thereby of the general formula I: ##SPC1##
wherein R represents hydrogen and lower alkyl; R' represents lower alkyl and formyl; by reacting, as the first step, the corresponding 2-substituted-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide (II) with a boron trifluoride compound and an acid anhydride IV; alternately, the starting material may be a 3-acetyl-2-substituted-2H-1,2-benzothiazin-4-[3H]-one 1,1-dioxide (III) which is reacted with the boron trifluoride compound, without the necessity for the acid anhydride (IV). Starting materials II and III subjected to step one of the process yield novel boron complex intermediates V (2,2-difluoro-4,5-disubstituted-2H-1,3,2-dioxaborino[5,4-c]-1,2-benzothiaz ine 6,6-dioxide). Boron complex intermediate V, in the second step of the process, is subjected to treatment with a Vilsmeier reagent (phosphorus oxychloride together with dimethylformamide), followed by hydrolysis. The substituted-pyrano[3,2-c][1,2]benzothiazine 6,6-dioxides of formula I prepared by the process of this invention have anti-secretory activity and are useful in the treatment of hyperacidity; certain of these compounds demonstrates anti-allergy activity.

REFERENCES:
patent: 3898218 (1975-08-01), Kaminsky

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