Synthesis of 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones or 1-hydroxy-1,6-dihydropylidine-2,5-diones from N-hydroxy-N-(2-oxoalkyl) amides

Synthesis of 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones or 1-hydroxy-1,6-dihydropylidine-2,5-diones from N-hydroxy-N-(2-oxoalkyl) amides Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2015, Volume: 56, Number: 44, Pages: 5980-5981 Pages count : DOI: 10.1016/j.tetlet.2015.09.030

Tags

Hydroxamic acid; Intramolecular cyclization; Oxidation reaction; 1,5-Dihydro-2H-pyrrol-2-ones; 1,6-Dihydropyridine-2,5-diones

Authors

Kulakov Ivan V. ¹ , Nikolaenkova Elena B. ² , Gatilov Yuri V. ^2,3 , Tikhonov Alexsei Ya. ² , Fisyuk Alexander S. ^1,4

Affiliations

1	(Данные Web of science) Omsk FM Dostoevsky State Univ, Dept Organ Chem, Omsk 644077, Russia
2	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
4	(Данные Web of science) Omsk State Tech Univ, Lab New Organ Mat, Omsk 644050, Russia

Efficient methods for the preparation of 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones and 1-hydroxy-1,6-dihydropyridine-2,5-diones from N-hydroxy-N-(2-oxoalkyl)amides are reported. It was found that the reaction of N-hydroxy-N-(2-oxoalkyl)amides with 3 equiv of potassium tert-butoxide led to 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones. A decrease of the base content to 1.5 equiv or less led to an increase of 1-hydroxy-3-phenyl-1,6-dihydropyridine-2,5-dione in the reaction due to oxidation of the starting materials by atmospheric oxygen and their subsequent transformation. (C) 2015 Elsevier Ltd. All rights reserved.

Kulakov I.V. , Nikolaenkova E.B. , Gatilov Y.V. , Tikhonov A.Y. , Fisyuk A.S.
Synthesis of 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones or 1-hydroxy-1,6-dihydropylidine-2,5-diones from N-hydroxy-N-(2-oxoalkyl) amides
Tetrahedron Letters. 2015. V.56. N44. P.5980-5981. DOI: 10.1016/j.tetlet.2015.09.030 WOS Scopus РИНЦ

Published print:

Oct 1, 2015

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