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KMID : 0043319900130030257
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Archives of Pharmacal Research
1990 Volume.13 No. 3 p.257 ~ p.260
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Synthesis of Methyl 2,6-Dimethyl-5-(1’’,2’’-Dioxo-2’’-Ethoxyethyl)-4-(3’’-Nitrophenyl)-1,4-Dihydropyridine-3-Carboxylate
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Suh JJ
Hong YH
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Abstract
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Hantzch’’s type reaction of methyl acetopyruvate (2a), methyl 3-aminocrotonate (3) and 3-nitrobenzaldehyde (4) led to dimethyl 3-acetyl-6-methyl-4-(3’’-nitrophenyl)-2,5-dicarboxylate (5a) and methyl 2,6-dimethyl-5-(1’’,2’’-dioxo-2’’-methoxyethyl)-4-(3’-nitrophenyl)-1,4-dihydropyridine-3-carboxylate (6a) in 26.7 and 9.2% yield, respectively. On the other hand, methyl 2,6-dimethyl-4-(3’’-nitrophenyl)-1,4-dihydropyridine 3-carboxylate (9) was acylated by ethyl oxaly chloride to give methyl 2,6-dimethyl-5-(1’’,2’’-dioxo-2’’-ethoxyethyl)-4-(3’’-nitrophenyl)-1,4-dihydropyridine-3-carboxylate (6b) in 76.8% yield.
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