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Molbank
Volume 2022
Issue 4
10.3390/M1460
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Short Note

3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

by
Carlotta Borgarelli
,
Stijn Lenaers
,
Wim M. De Borggraeve
and
Ermal Ismalaj
*
Department of Chemistry, Molecular Design and Synthesis, KU Leuven Campus Arenberg Celestijnenlaan 200F–Box 2404, 3001 Leuven, Belgium
*
Author to whom correspondence should be addressed.
Molbank 2022, 2022(4), M1460; https://doi.org/10.3390/M1460
Submission received: 7 September 2022 / Revised: 29 September 2022 / Accepted: 30 September 2022 / Published: 9 October 2022
(This article belongs to the Collection Heterocycle Reactions)
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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.
Keywords: 1,4-dihydropyridine; LTCC; tosylation; building blocks; synthesis 1,4-dihydropyridine; LTCC; tosylation; building blocks; synthesis

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MDPI and ACS Style

Borgarelli, C.; Lenaers, S.; De Borggraeve, W.M.; Ismalaj, E. 3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. Molbank 2022, 2022, M1460. https://doi.org/10.3390/M1460

AMA Style

Borgarelli C, Lenaers S, De Borggraeve WM, Ismalaj E. 3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. Molbank. 2022; 2022(4):M1460. https://doi.org/10.3390/M1460

Chicago/Turabian Style

Borgarelli, Carlotta, Stijn Lenaers, Wim M. De Borggraeve, and Ermal Ismalaj. 2022. "3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate" Molbank 2022, no. 4: M1460. https://doi.org/10.3390/M1460

APA Style

Borgarelli, C., Lenaers, S., De Borggraeve, W. M., & Ismalaj, E. (2022). 3-Methyl 5-{3-[(4-Methylbenzenesulfonyl)oxy]propyl} 4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. Molbank, 2022(4), M1460. https://doi.org/10.3390/M1460

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