Alternative Synthesis of Isoguvacine and Its N-(2-Aryl-2-hydroxyethyl) Derivatives

Autor:	O. O. Zaporozhets, D. A. Lomov, M. G. Abramyants, S. N. Lyashchuk
Rok vydání:	2018
Předmět:	010405 organic chemistry Aryl Organic Chemistry Substituent 010402 general chemistry Ring (chemistry) Isonicotinic acid Phenacyl 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Acid hydrolysis Isoguvacine Benzene
Zdroj:	Russian Journal of Organic Chemistry. 54:593-600
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428018040139
Popis:	Isonicotinic acid ethyl ester reacted with substituted phenacyl bromides to give the corresponding quaternary salts which were reduced with sodium tetrahydridoborate to ethyl 1-(2-aryl-2-hydroxyethyl)-1,2,3,6- tetrahydropyridine-4-carboxylates. The presence of an electron-donating substituent in the benzene ring of the latter is a necessary condition for their acid hydrolysis with cleavage of the C–N bond and formation of isoguvacine. Analogous derivatives with electron-withdrawing substituents are not converted to isoguvacine under similar conditions.
Databáze:	OpenAIRE
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