Abstract
In the title compound, C14H15NO4S, the di-hydro-thia-zine ring adopts a distorted sofa conformation with the S atom displaced from the mean plane through the N and C ring atoms by 0.767 (1) Å. The allyl substituent (C-C=C) is inclined to this mean plane by 78.5 (7)° and the acetate group [C(=O)-O-C] by 66.5 (3)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions forming chains propagating along the a-axis direction.
Highlights
In the title compound, C14H15NO4S, the dihydrothiazine ring adopts a distorted sofa conformation with the S atom displaced from the mean plane through the N and C ring atoms by 0.767 (1) Å
Molecules are linked by C—H interactions forming chains propagating along the a-axis direction
It is quite difficult to predict their behaviour in the alkylation reactions of the esters of 4-methyl-2,2-dioxo-1H-26,1-benzothiazine-3-carboxylic acids, and the determination of the true structure is essential
Summary
Alkylation of nitrogen heterocycles, those containing reactive exocyclic groups, always attracts attention with its ambiguity and dependence on a variety of factors. Esters of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3carboxylic acids are primarily alkylated exclusively at the 4OH group (Ukrainets et al, 1996). Methyl 4-hydroxy-2,2-dioxo-1H-26,1-benzothiazine-3-carboxylates that are structurally close to them form mixtures of isomeric. 3-C- and 4-O-alkylation products under the same conditions (Ukrainets et al, 2015). It is quite difficult to predict their behaviour in the alkylation reactions of the esters of 4-methyl-2,2-dioxo-1H-26,1-benzothiazine-3-carboxylic acids, and the determination of the true structure is essential. It has been found that methyl 4-methyl-2,2-dioxo-1H-26,1benzothiazine-3-carboxylate 1 in the K2CO3/DMSO system is rapidly alkylated with allyl bromide 2 by the cyclic nitrogen atom, with formation of the main product of the reaction studied viz. It has been found that methyl 4-methyl-2,2-dioxo-1H-26,1benzothiazine-3-carboxylate 1 in the K2CO3/DMSO system is rapidly alkylated with allyl bromide 2 by the cyclic nitrogen atom, with formation of the main product of the reaction studied viz. compound 3 (see Fig. 1)
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