New synthetic approaches to 3-carhoxamides of 4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide

Two new synthetic approaches to the title compounds are reported. In the first of these, starting with N-carbobenzyloxysarcosine, four synthetic steps are employed to finally assemble the C³? C⁴ bond of the 1,2-benzothiazine ring. In the second approach, an enol ether is employed as a protecting group to allow formation of the 3-carboxamide function, which is followed by cleavage of the ether function to yield the desired 4-hydroxy-1,2-benzothiazine-3-carboxamide 1,1-dioxide.