Synthesis of 3‐Haloisoxazolines by Deoxygenation of 3‐Haloisoxazoline N‐Oxides under Treatment with Acetyl Bromide

Synthesis of 3‐Haloisoxazolines by Deoxygenation of 3‐Haloisoxazoline N‐Oxides under Treatment with Acetyl Bromide Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2022, Volume: 7, Number: 27, Article number : e202202267, Pages count : DOI: 10.1002/slct.202202267

Authors

Fadeeva Anastasia A. ^1,2 , Ioffe Sema L. ¹ , Tabolin Andrey A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991 Russia
2	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow, 125047 Russia

A method for the preparation of 4,5-disubstituted 3-halo- (chloro-, bromo-) isoxazolines was developed. Acetyl bromide was found to be a convenient reducing agent for 3-halosubstituted isoxazoline N-oxides affording target deoxygenated derivatives in good yields. Compared to the literature examples, presented approach for the synthesis of 3-haloisoxazolines is regioselective and does not require the use of hazardous phosgene oximes. Selective transformations of the obtained products were demonstrated.

Fadeeva A.A. , Ioffe S.L. , Tabolin A.A.
Synthesis of 3‐Haloisoxazolines by Deoxygenation of 3‐Haloisoxazoline N‐Oxides under Treatment with Acetyl Bromide
ChemistrySelect. 2022. V.7. N27. e202202267 . DOI: 10.1002/slct.202202267 WOS Scopus OpenAlex

≡ Web of science:	WOS:000825292000001
≡ Scopus:	2-s2.0-85134491800
≡ OpenAlex:	W4285594685