YAKHAK HOEJI (약학회지)
- Volume 33 Issue 5
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- Pages.290-295
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- 1989
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- 0377-9556(pISSN)
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- 2383-9457(eISSN)
Synthesis of 1,4-Dihydropyridine-5-Formyl Derivatives
1,4-Dihydropyridine-5-Formyl 유도체의 합성
- Hong, You-Hwa (Yuhan Research Center) ;
- Suh, Jung-Jin (Yuhan Research Center)
- Published : 1989.10.28
Abstract
2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (1) was formylated to 2,6-dimethy-4-(3'-nitrophenyl)-5-formyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (2) in 76% yield. At the elevated temperature, 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-monomethyl ester (3) was also converted into compound 2 in 46% yield. The compound 2 was reduced to 2,6-dimethyl-4-(3'-nitrophenyl)-5-hydroxymethyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (4) in 91% yield. Compound 2 was reacted with triethyl phosphonoacetate to give 2,6-dimethyl-4-(3'-nitrophenyl)-5-(2-ethoxycarbonyl ethenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (5) in 50% yield. Reaction between compound 2 and amines (methyl amine, ethylamine, methoxylamine, hydroxyl amine, phenyl hydrazine and 1-amino-4-methyl piperazine) gave six schiff bases 7a, 7b, 7c, 7e, 7f in 81%, 91%, 82%, 81%, 50% and 84% yield, respectively.
Keywords
- 1,4-dihydropyridine;
- formylation;
- 2,6-dimethyl-4-(3'-nitrophenyl)-5-formyl-1,4-dihydropyridine-3-carboxylic acid methyl ester;
- reduction;
- horner-wadsworth-emmons reaction;
- schiff bases