A new class of enehydroxylamino ketones - (R)-2-(1-hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and reactions

A new class of enehydroxylamino ketones - (R)-2-(1-hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and reactions Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2004, Volume: 2004, Number: 4, Pages: 749-765 Pages count : 17 DOI: 10.1002/ejoc.200300536

Tags

enaminones; EPR spectroscopy; imidazolidines; ketones; nitroxides; nucleophilic substitution

Authors

Reznikov VA ¹ , Roshchupkina GI ² , Mazhukin DG ¹ , Petrov PA ³ , Popov SA ³ , Fokin SV ³ , Romanenko GV ³ , Rybalova TV ¹ , Gatilov YV ¹ , Shvedenkov YG ³ , Irtegova IG ¹ , Shundrin LA ⁴ , Ovcharenko VI ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, 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
4	(Данные Web of science) Russian Acad Sci, Siberian Branch, Novosibirsk Bioorgan Chem Inst, Novosibirsk 630090, Russia

Three approaches to the synthesis of (R)-2-(1-hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones 1 are described: (a) condensation of 1,2-bishydroxyla mines with fiketoaldehyde synthons, (b) treatment of metallated 1-hydroxy-2-methyl-4,5-dihydroimidazoles with esters, and (c) 1,3-dipolar cycloaddition between 1-hydroxy-4,5-dihydroimidazole-3-oxide and DMAD. The reactivity of I with electrophiles has been studied. The exocyclic methylene (enamine) carbon atom is shown to be the major site of electrophilic attack. Synthesized chloro-substituted 1-hydroxy-2acetylideneimidazolidines react with sodium cyanide to form the corresponding nitriles. Oxidation of these nitriles occurs with formation of persistent vinyl nitroxides, which are of interest as potential paramagnetic ligands. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Reznikov V. , Roshchupkina G. , Mazhukin D. , Petrov P. , Popov S. , Fokin S. , Romanenko G. , Rybalova T. , Gatilov Y. , Shvedenkov Y. , Irtegova I. , Shundrin L. , Ovcharenko V.
A new class of enehydroxylamino ketones - (R)-2-(1-hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and reactions
European Journal of Organic Chemistry. 2004. V.2004. N4. P.749-765. DOI: 10.1002/ejoc.200300536 WOS Scopus РИНЦ

Published print:

Feb 1, 2004

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