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Ring contraction of 3-carboxamide or 3-carboxylate of 4-hydroxy-2- methyl-2H-1,2-benzothiazine-1,1-dioxide and analogous 1 (2H)-isoquinolinone- 3-carboxylate
Khalaj, Ali,Adibpour, Neda
, p. 131 - 135 (2007/10/03)
A novel ring transformation of 3-carboxylate or 3-carboxamide of 4- hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide and analogous 1(2H)- isoquinolinone-3-carboxylate to the 5-membered rings upon the reaction with carbonyl compounds in the presence of primary or secondary amines is described.
Process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
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, (2008/06/13)
A process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, which may be used as a non-steroidal analgesic and anti-inflammatory drug. The process comprises reacting saccharin sodium with isopropyl chloroacetate in dimethylformamide, reacting the resultant isopropyl 3-oxo-1,2-benzoisothiazoline-2-acetate 1,1-dioxide with sodium isopropylate in isopropanol to produce an intermediate which, when methylated in an aqueous-alcoholic basic medium with dimethyl sulfate, gives an intermediate compound which when condensed with 2-aminopyridine in xylene, yields 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazone-3-carboxamide 1,1-dioxide.