Reactivity of oximes of 1-aryl(hetaryl)-2-(hydroxyamino)propan-1-ones with ethyl glyoxylate

Reactivity of oximes of 1-aryl(hetaryl)-2-(hydroxyamino)propan-1-ones with ethyl glyoxylate Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2019, Volume: 55, Number: 2, Pages: 142-146 Pages count : 5 DOI: 10.1007/s10593-019-02430-8

Tags

esters of 5-hydroxy-3-aryl-5; 6-dihydro-4H-1; 2; 5-oxadiazine-6-carboxylic acid; esters of 1-hydroxy-1H-imidazole-2-carboxylic acids; ethyl glyoxylate; hydroxyamino oximes

Authors

Nikolaenkova Elena B. ¹ , Tikhonov Alexei Ya. ¹ , Grishchenko Stanislav Yu. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia

iAlkyl(hetero)aromatic -hydroxyamino oximes with the anti configuration of the oxime group reacted with ethyl glyoxylate to form 5-aryl(hetaryl)-1-hydroxy-1H-imidazole-2-carboxylic acid ethyl esters. In the case of 4-fluorophenyl-, 4-chlorophenyl-, and 4-methoxyphenyl-substituted -hydroxyamino oximes, 3-aryl-5-hydroxy-5,6-dihydro-4H-1,2,5-oxadiazine-6-carboxylic acid ethyl esters were also formed. The positions of the substituents in the imidazole ring were established on the basis of a comparative analysis of the spectroscopic data of these products and the synthesized isomeric compound, 1-hydroxy-5-methyl-4-phenyl-1H-imidazole-2-carboxylic acid ethyl ester. 5-Aryl(hetaryl)-1H-imidazole-2-carboxylic acids were obtained in the reaction of 5-aryl(hetaryl)-1-hydroxy-1H-imidazole-2-carboxylic acids ethyl esters with chloroacetone.

Nikolaenkova E.B. , Tikhonov A.Y. , Grishchenko S.Y.
Reactivity of oximes of 1-aryl(hetaryl)-2-(hydroxyamino)propan-1-ones with ethyl glyoxylate
Chemistry of Heterocyclic Compounds. 2019. V.55. N2. P.142-146. DOI: 10.1007/s10593-019-02430-8 WOS Scopus РИНЦ

Published print:	Feb 1, 2019
Published online:	Mar 20, 2019

Web of science	WOS:000463779400005
Scopus	2-s2.0-85063991423
Elibrary	38672282
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