REACTIVITY OF OXIMES OF 1-ARYL(HETARYL)-2-(HYDROXYAMINO)PROPAN-1-ONES WITH ETHYL GLYOXYLATE

Authors

  • Елена Б. Николаенкова N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Алексей Я. Тихонов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Станислав Ю. Грищенко N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090

DOI:

https://doi.org/10.1007/4786

Keywords:

гидроксиаминооксимы, этиловый эфир глиоксиловой кислоты, эфиры 1-гидрокси-3-арил-5, 6-дигидро-4Н-1, 2, 5-оксадиазин-6-карбоновых кислот, эфиры 1-гидрокси-1Н-имидазол-2-карбоновых кислот

Abstract

Alkyl(hetero)aromatic α-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 α-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.

Authors: Elena B. Nikolaenkova, Alexei Ya. Tikhonov*, Stanislav Yu. Grishchenko

Author Biography

Елена Б. Николаенкова, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090

д.х.н., доцент, г.н.с. Лаборатории гетероциклических соединений (ЛГЦС)

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Published

2019-03-11

Issue

Vol. 55 No. 2 (2019)

Section

Original Papers