Author:

Keywords:

1SB6521N|1SB6523N#55976436, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, 1, 4-dihydropyridine, LTCC, tosylation, building blocks, synthesis, CALCIUM-CHANNEL BLOCKERS, 1,4-DIHYDROPYRIDINES, HYPERTENSION, DERIVATIVES, DRUGS, SAR, 3401 Analytical chemistry, 3404 Medicinal and biomolecular chemistry

Abstract:

The 1,4-dihydropyridine is a ubiquitous scaffold employed not only in medicinal chemistry but also in organic synthesis, given its ability to act as a hydrogen transfer reagent, thus emulating NAD(P)H reducing agents. In this work, we describe the synthesis of 3-methyl 5-{3-[(4-methylbenzenesulfonyl)oxy]propyl} 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as scaffold, which enables downstream derivatization towards new 1,4-dihydropyridine molecules. Inspired by the literature, a new two-step synthesis was planned that involved: (i) synthesis of a silylated 1,4-dihydropyridine derivative and (ii) deprotection and tosylation in one step using tosyl fluoride.