Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3-Halo-1,2-Oxazines

Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3-Halo-1,2-Oxazines Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 21, Pages: 13794-13806 Pages count : 13 DOI: 10.1021/acs.joc.9b02010

Authors

Malykhin Roman S. ^1,2 , Kokuev Aleksandr O. ^3,1 , Dorokhov Valentin S. ^3,1 , Nelyubina Yulia V. ⁴ , Tartakovsky Vladimir A. ¹ , Tabolin Andrey A. ¹ , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ^3,1,5

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow, Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, 119991, Leninskie gory, 1, str. 3, Moscow, Russian Federation
3	D. Mendeleev University of Chemical Technology of Russia, 125047, Miusskaya sq., 9, Moscow, Russian Federation
4	A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Vavilov str., 28, Moscow, Russian Federation
5	Plekhanov Russian University of Economics, 117997, Stremyanny per., 36, Moscow, Russian Federation

In this article, comprehensive studies on the nucleophilic chlorination and bromination of readily available six-membered cyclic nitronates (1,2-oxazine-N-oxides) are reported. Under optimized conditions (POCl3 or (COBr)2 with Hünig’s base), 3-halo-substituted 1,2-oxazines, which are difficult to access by other routes, were obtained in good to high yields. The latter were shown to be convenient precursors to other 3-substituted 1,2-oxazine derivatives using Lewis/Brønsted acid-assisted substitution of the halide atom for C-, S-, and N-nucleophiles.

Malykhin R.S. , Kokuev A.O. , Dorokhov V.S. , Nelyubina Y.V. , Tartakovsky V.A. , Tabolin A.A. , Ioffe S.L. , Sukhorukov A.Y.
Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3-Halo-1,2-Oxazines
Journal of Organic Chemistry. 2019. V.84. N21. P.13794-13806. DOI: 10.1021/acs.joc.9b02010 WOS Scopus OpenAlex

Web of science:	WOS:000494562600052
Scopus:	2-s2.0-85074232593
OpenAlex:	W2980013533

DB	Citing
OpenAlex	10
Scopus	10
Web of science	10