Reversible pH-dependent cyclization of hydroxy-substituted gem-chloronitroso compounds to isoxazoline N-oxides and 5,6-dihydro-4H-1,2-oxazine N-oxides

Reversible pH-dependent cyclization of hydroxy-substituted gem-chloronitroso compounds to isoxazoline N-oxides and 5,6-dihydro-4H-1,2-oxazine N-oxides Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 5, Pages: 1303-1311 Pages count : 9 DOI: 10.1007/s11172-024-4247-1

Authors

Malykhin R.S. ¹ , Sukhorukov A.Yu. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Cyclization of hydroxy-substituted gem-chloronitroso compounds under the action of bases affords cyclic nitronates, namely, isoxazoline N-oxides and 5,6-dihydro-4H-1,2-oxazine N-oxides. The process is reversible, viz., the chloronitroso compounds are regenerated upon the action of hydrogen chloride on the cyclization products. A method for the synthesis of cyclic nitronates from aldols using the title reaction was developed. The cyclization mechanism was studied and the kinetic parameters of the process were determined using UV—Vis and IR monitoring and the results of quantum chemical calculations.

Malykhin R.S. , Sukhorukov A.Y.
Reversible pH-dependent cyclization of hydroxy-substituted gem-chloronitroso compounds to isoxazoline N-oxides and 5,6-dihydro-4H-1,2-oxazine N-oxides
Russian Chemical Bulletin. 2024. V.73. N5. P.1303-1311. DOI: 10.1007/s11172-024-4247-1 WOS Scopus OpenAlex

Web of science:	WOS:001252371600020
Scopus:	2-s2.0-85196478687
OpenAlex:	W4399899492

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