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SYNTHESIS AND HYDROLYSIS OF ETHOXYCARBONYLMETHYL AND CYANOETHYL 5-CYANO-6-METHYLSULFANYL-1,4-DIHYDROPYRIDINE- 3-CARBOXYLATES UND Synthese und Hydrolyse Ethoxycarbonylmethyl Cyanoethyl-6-5-Cyano-1 ,4-dihydropyridin-methylsulfanyl 3-Carboxylate

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Author(s): Z.Andzans, A.Krauze, L.Bekere, S.Grinberga, I.Adlere, G.Duburs

Journal: Heterocyclic Letters
ISSN 2231-3087

Volume: 1;
Issue: 3;
Start page: 197;
Date: 2011;
Original page

Keywords: Ethoxycarbonylmethyl 6-methylsulfanyl-1 | 4-dihydropyridine-3-carboxylates; 2-cyanoethyl 6-methylsulfanyl-1 | 4-dihydropyridine-3-carboxylates; one-pot four-component synthesis; hydrolysis; alkylation; Candida antarctica lipase B.

ABSTRACT
Ethoxycarbonylmethyl and 2-cyanoethyl 6-methylsulfanyl-1,4-dihydropyridine- 3-carboxylates were synthesized by making use of one-pot four- and five-component method, and by alkylation of 1,4-dihydropyridine-3-carboxylic acid with ethyl bromoacetate. By basic hydrolysis of esters, both 1,4-dihydropyridine-3-carboxylic acids and (1,4-dihydropyridine- 3-carbonyloxy)acetic acids were prepared. Candida antarctica lipase B catalysed hydrolysis of ethoxycarbonylmethyl 1,4-dihydropyridine-3-carboxylates proceeded with low enantioselectivity yielding both type of acids as slightly enantioenriched compounds.
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