3-Nitrobenzaldehyde → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-benzyloxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine

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Reaction Steps

The ω-phenylalkylacetoacetate derivative (5) is then reacted with an alkyl β-aminocrotonate (or methoxyethyl β-aminocrotonate depending on the desired R5) and a benzaldehyde derivative (depending on the desired R4, e.g. for compounds in which R4 is meta --NO2, 3-nitrobenzaldehyde is used) under Hantzsch Dihydropyridine synthesis conditions (see, e.g., Fox, et al., J. Org. Chem., 16, 1259 (1951)) to form a 4-phenyl-2,5-dimethyl-1,4-dihydropyridine dicarboxylate diester (6). For example, 2-[4-(2-benzyloxyethoxy)phenyl]ethylacetoacetate (5) is reacted with methyl β-aminocrotonate and 3-nitrobenzaldehyde to produce 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-benzyloxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine (Step 6).

Provenance & Evidence