790271-53-3Relevant academic research and scientific papers
A novel approach to pyrrolo[2,1-b][1,3]benzothiazines
Tverdokhlebov, Anton V.,Andrushko, Alexander P.,Tolmachev, Andrey A.,Shishkina, Svitlana V.,Shishkin, Oleg V.
experimental part, p. 2701 - 2706 (2009/04/04)
Alkylation of (3,4-dihydro-4-oxo-2H-1,3-benzothiazin-2-ylidene)acetic acid ethyl ester and (3,4-dihydro-4-oxo-2H-1,3-benzothiazin-2-ylidene)acetonitrile with phenacyl chlorides in the presence of potassium carbonate was shown to occur at the nitrogen atom yielding the corresponding N-phenacyl derivatives. The latter, upon treatment with DMF·POCl3 complex, were converted into 1-aroyl-9-oxo-9H-pyrrolo[2,1 b][1,3]benzothiazine-3-carboxylic acid ethyl esters and -3-carbonitriles. The structure of the obtained pyrrolobenzothiazine derivatives was confirmed unambiguously by X-ray crystallographic study. Reaction of these pyrrolo[2,1-b][1,3]benzothiazines with aliphatic primary amines resulted in the thiazine ring cleavage and formation of 2-[(5-aroyl-3-cyano(or ethoxycarbonyl)-1H-pyrrol-2-yl)thio]-N- alkylbenzamides. Georg Thieme Verlag Stuttgart.
