Synthesis of 4H-imidazole-5-carbaldoxime 3-oxides and 4H-imidazole-5-carbonitrile 3-oxides

Synthesis of 4H-imidazole-5-carbaldoxime 3-oxides and 4H-imidazole-5-carbonitrile 3-oxides Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2008, Volume: 57, Number: 7, Pages: 1516-1533 Pages count : DOI: 10.1007/s11172-008-0196-3

Tags

alpha-hydroxyamino ketones; 4H-imidazole 3-oxides; nitrosation; nitrones; 2,5-dihydroimidazoles

Authors

Kirilyuk I. A. , Morozov D. A. , Tabatchikova Yu. S. , Medvedev V. S. , Lebedev A. V. , Romanenko G. V. , Rybalova T. V. , Grigor'ev I. A.

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, Int Tomog Ctr, Novosibirsk 630090, Russia

The condensation of 3-hydroxyamino-3-methylbutan-2-one or 3-ethyl-3-hydroxyamino-pentan-2-one with aldehydes and ammonia afforded a series of new 1-hydroxy-4-methyl-2,5-dihydroimidazoles, whose oxidation gave rise to the corresponding 5-methyl-4H-imidazole 3-oxides. The latter, like 1-hydroxy-4-methyl-2,5-dihydroimidazoles, react with Pr(i)ONO in the presence of bases to form 4H-imidazole-5-carbaldoxime 3-oxides, which are transformed into 4H-imidazole-5-carbonitrile 3-oxides in the reaction with TsCl in the presence of Et(3)N. The by-products produced in different steps of the synthesis were isolated and characterized.

Kirilyuk I.A. , Morozov D.A. , Tabatchikova Y.S. , Medvedev V.S. , Lebedev A.V. , Romanenko G.V. , Rybalova T.V. , Grigor'ev I.A.
Synthesis of 4H-imidazole-5-carbaldoxime 3-oxides and 4H-imidazole-5-carbonitrile 3-oxides
Russian Chemical Bulletin. 2008. V.57. N7. P.1516-1533. DOI: 10.1007/s11172-008-0196-3 WOS Scopus РИНЦ OpenAlex

Кирилюк И.А. , Морозов Д.А. , Табатчикова Ю.С. , Медведев В.С. , Лебедев А.В. , Романенко Г.В. , Рыбалова Т.В. , Григорьев И.А.
Синтез 4h-имидазол- 5 -карбальдоксим-3 -оксидов и 4h-имидазол-5-карбонитрил-3-оксидов
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2008. №7. С.1487-1503. РИНЦ

Published print:	Jul 1, 2008
Published online:	May 27, 2009

Web of science:	WOS:000266456700023
Scopus:	2-s2.0-67650457596
Elibrary:	13597758
OpenAlex:	W1973382442

DB	Citing
Web of science	2
Scopus	2
Elibrary	2
OpenAlex	2