Reaction of 2-alkoxypropenals with alpha-hydroxyamino oximes and 1,2-bis(hydroxyamino)cyclohexane

Reaction of 2-alkoxypropenals with alpha-hydroxyamino oximes and 1,2-bis(hydroxyamino)cyclohexane Научная публикация

Журнал

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Вых. Данные

Год: 2005, Том: 41, Номер: 10, Страницы: 1421-1429 Страниц : 9 DOI: 10.1007/s11178-005-0361-1

Авторы

Keiko NA ¹ , Funtilkova EA ¹ , Larina LI ¹ , Sarapulova GI ¹ , Mazhukin AG ² , Rybajova TV ² , Tikhonov AY ²

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Div, Favorskii Irkutsk Inst Chem, Irkutsk 664033, Russia
2	(Данные Web of science) Russian Acad Sci, Siberian Div, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

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.

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

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

Опубликована в печати:

1 окт. 2005 г.

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