Abstract: Reactions of 2-alkoxypropenals with alpha-hydroxyamino oximes in neutral medium involve the aldehyde group of the former to afford both acyclic and cyclic azomethine oxides: N-(2-hydroxyiminoalkyl)-N-(2-alkoxy-2-propenylidene)amine oxides and 1-hydroxy-2,5-dihydroimidazole 3-oxides. The state of tautomeric equilibrium between the cyclic and acyclic products depends on the solvent nature and temperature. The reaction in acidic aqueous medium is accompanied by hydrolysis of the vinyl ether moiety in 2-alkoxypropenals with formation of 2-oxopropionaldehyde which reacts with alpha-hydroxyamino oxime at the hydroxyamino group to give substituted pyrazine 1,4-dioxides. The reaction of 2-alkoxypropenals with 1,2-bis(hydroxyamino)cyclohexane leads to formation of 2-(1-alkoxyvinyl)-1,3-dihydroxyperhydrobenzimidazoles. The structure of the products was proved by IR, UV, and H-1 and C-13 NMR spectroscopy and X-ray analysis.

Cite: Keiko N. , Funtilkova E. , Larina L. , Sarapulova G. , Mazhukin A. , Rybajova T. , Tikhonov A.
Reaction of 2-alkoxypropenals with alpha-hydroxyamino oximes and 1,2-bis(hydroxyamino)cyclohexane
Russian Journal of Organic Chemistry. 2005. V.41. N10. P.1421-1429. DOI: 10.1007/s11178-005-0361-1 WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Кейко Н.А. , Фунтикова Е.А. , Ларина Л.И. , Сарапулова Г.И. , Мажукин Д.Г. , Рыбалова Т.В. , Тихонов А.Я.
Взаимодействие 2-алкоксипропеналей с 1,2-гидроксиламинооксимами и 1,2-бисгидроксиаминоциклогексаном
Журнал органической химии (RUSS J ORG CHEM+). 2005. Т.41. №10. С.1453-1461. РИНЦ

Dates:

Published print:

Oct 1, 2005

Identifiers:

Web of science	WOS:000234156900003
Scopus	2-s2.0-29244455301
Elibrary	13495938
OpenAlex	W2952409311

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