Abstract
Synthesis of isoquinolines substituted with pyrimidine in 1-position was attempted since no such compounds seem to have been prepared. The starting materials prepared were 2-phenyl- (Ia), 2-o-tolyl- (Ib), and 2-p-tolyl-4-methyl-5-pyrimidinecarbonyl chloride (Ic), 2-p-tolyl-4-methyl-5-pyrimidinecarbonylazide (IIc), and 2-p-tolyl-4-methyl-5-ethoxycarbonylpyrimidine (IIIc). Condensation of (Ia) and homopiperonylamine (IV) afforded the corresponding acid amide (VIa), and condensation of (Ia), (Ib), (Ic), (IIc), and (IIIc) with α-methyl-β-(3, 4-methylenedioxyphenyl) ethylamine (V) also afforded the corresponding acid amides (VIIIa, b, c). These amides (VIa, VIIIa, b, c) were submitted to isoquinoline cyclization by the Bischler-Napieralski reaction and the objective isoquinolines (VIIa, IXa, b, c) were obtained, although in somewhat poor yield.
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Schedule a callMore From: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
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