Transformations of conjugated enamines of the imidazolidine 1-oxide series in the Vilsmeier-Haack reaction

Transformations of conjugated enamines of the imidazolidine 1-oxide series in the Vilsmeier-Haack reaction Full article

Journal

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

Output data

Year: 2007, Volume: 56, Number: 6, Pages: 1210-1215 Pages count : 6 DOI: 10.1007/s11172-007-0183-0

Tags

nitroxides; enaminones; nitroenamine; Vilsmeier-Haack reaction; imidazolidines

Authors

Becker Ch.S. ¹ , Roshchupkina G.I. ² , Rybalova T.V. ² , Gatilov Yu.V. ² , Reznikov V.A. ²

Affiliations

1	Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation
2	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

In some cases, the reactions of enaminones of the imidazolidine 1-oxide series with the Vilsmeier reagent afford electrophilic substitution products containing the dimethyl-aminomethylene group. In an acidic medium, these products undergo either hydrolytic elimination of the dimethylaminomethylene moiety or hydrolysis of the latter to form the aldehyde group. The reaction of nitroenamine, which is a derivative of imidazolidine 1-oxide, with the Vilsmeier reagent produces furoxane, viz., the nitroxyl biradical. Reduction of the latter affords the dioxime biradical.

Becker C.S. , Roshchupkina G.I. , Rybalova T.V. , Gatilov Y.V. , Reznikov V.A.
Transformations of conjugated enamines of the imidazolidine 1-oxide series in the Vilsmeier-Haack reaction
Russian Chemical Bulletin. 2007. V.56. N6. P.1210-1215. DOI: 10.1007/s11172-007-0183-0 WOS Scopus РИНЦ

Мельникова-Беккер К.С. , Рощупкина Г.И. , Рыбалова Т.В. , Гатилов Ю.В. , Резников В.А.
Превращения сопряженных енаминов ряда имидазолидин-1-оксила в реакции Вильсмайера-Хаака
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2007. №6. С.1165-1170.. РИНЦ

Published print:

Jun 1, 2007

Web of science	WOS:000251971700018
Scopus	2-s2.0-36949002086
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