Abstract
A new synthesis of 2-phenylpyrano[3,2-b]phenothiazin-4(6H)-one derivatives was reported. First 2,10-diacetyl-3-hydroxyphenothiazine (2) was converted into their benzoyloxy esters (3a–3j) using different aromatic carboxylic acids in the presence of phosphorous oxychloride in pyridine. Benzoyloxy esters were converted into their 1,3-diones (4a–4j) by using dry KOH in pyridine via Baker-Venkataraman transformation reaction. The 1,3-diones thus obtained were cyclised to pyranophenothiazines (5a–5j) by refluxing in an acetic acid/HCl mixture.
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