Tandem Deoxygenation/Halogenation of N -Oxides Under Acylation Conditions: Scope and In Situ IR Spectroscopic Study

Tandem Deoxygenation/Halogenation of N -Oxides Under Acylation Conditions: Scope and In Situ IR Spectroscopic Study Full article

Journal

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

Output data

Year: 2019, Volume: 2019, Number: 26, Pages: 4139-4148 Pages count : 10 DOI: 10.1002/ejoc.201900131

Authors

Malykhin Roman S. ^1,2 , Golovanov Ivan S. ¹ , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ^3,1,4

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect, 47, 119991 Moscow, Russia
2	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, 1, str. 3, 119991 Moscow, Russia
3	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047 Moscow, Russia
4	Plekhanov Russian University of Economics, Stremyanny per. 36, 117997 Moscow, Russia

Acylation of cyclic nitronates with acyl bromides produces 3-bromomethyl-substituted 5,6-dihydro-2H-1,2-oxazines via an unusual multi-stage process involving deoxygenation of N-oxide and the formation of Br2. Low-temperature in situ ATR FT-IR monitoring and DFT calculations revealed α-halo-substituted N,N-bis(oxy)amines as key intermediates of the process. The developed method was successfully exploited in the stereoselective synthesis of pharmaceutically relevant molecules.

Malykhin R.S. , Golovanov I.S. , Ioffe S.L. , Sukhorukov A.Y.
Tandem Deoxygenation/Halogenation of N -Oxides Under Acylation Conditions: Scope and In Situ IR Spectroscopic Study
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4139-4148. DOI: 10.1002/ejoc.201900131 WOS Scopus OpenAlex

Web of science:	WOS:000475679400007
Scopus:	2-s2.0-85063566497
OpenAlex:	W2919776421

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OpenAlex	5
Scopus	5
Web of science	5