1,4-Dihydropyridine-5-Formyl 유도체의 합성

• 영문명: Synthesis of 1,4-Dihydropyridine-5-Formyl Derivatives
• 발행기관: 대한약학회
• 저자명: 홍유화(You Hwa Hong) 서정진(Jung Jin Suh)
• 간행물 정보: 『약학회지』제33권 제5호 (1989년), 290~295쪽, 전체 6쪽
• 주제분류: 의약학 > 기타의약학
• 파일형태: PDF
• 발행일자: 1989.10.28

영문 초록

2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (1) was formulated to 2,6-dimethyl-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 (methylamine, ethylamine, methoxylamine, hydroxylamine, 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.

키워드

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.