Metal-assisted addition of a nitrate anion to bis(oxy)enamines. A general approach to the synthesis of α-nitroxy-oxime derivatives from nitronates

Metal-assisted addition of a nitrate anion to bis(oxy)enamines. A general approach to the synthesis of α-nitroxy-oxime derivatives from nitronates Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2016, Volume: 14, Number: 16, Pages: 3963-3974 Pages count : 12 DOI: 10.1039/c6ob00388e

Authors

Naumovich Yana A. ¹ , Buckland Victoria Emily ² , Sen'ko Dmitry A. ³ , Nelyubina Yulia V. ⁴ , Khoroshutina Yulia A. ¹ , Sukhorukov Alexey Yu. ¹ , Ioffe Sema L. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia
2	National Junior College, Hillcrest Road 37, 288913, Singapore
3	Moscow Chemical Lyceum, Tamozhenniy proezd 4, 111033 Moscow, Russia
4	A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilov str. 28, 119991 Moscow, Russia

The synthesis of α-nitroxy-substituted oxime derivatives has been achieved by an unprecedented metal-assisted addition of a nitrate anion to bis(oxy)enamines, which are readily available from nitronates or nitroalkanes. The method has a broad scope and provides access to α-nitroxy-oximes and their cyclic ethers including nitroxy-substituted isoxazolines and dihydro-1,2-oxazines, which are of interest as potential NO-donors and intermediates in the synthesis of bioactive molecules.

Naumovich Y.A. , Buckland V.E. , Sen'ko D.A. , Nelyubina Y.V. , Khoroshutina Y.A. , Sukhorukov A.Y. , Ioffe S.L.
Metal-assisted addition of a nitrate anion to bis(oxy)enamines. A general approach to the synthesis of α-nitroxy-oxime derivatives from nitronates
Organic & Biomolecular Chemistry. 2016. V.14. N16. P.3963-3974. DOI: 10.1039/c6ob00388e WOS Scopus OpenAlex

Web of science:	WOS:000374786500015
Scopus:	2-s2.0-84969219503
OpenAlex:	W2335542192

DB	Citing
OpenAlex	27
Scopus	26
Web of science	26