Synthesis of bicyclic systems containing fused sulfolane and isoxazolidine rings

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 54; no. 1; pp. 76 - 82
• Main Authors: Berestovitskaya, Valentina M., Efremova, Irina E., Serebryannikova, Anna V., Lapshina, Lidiya V., Gurzhiy, Vladislav V.
• Format: Journal Article
• Language: English
• Published: New York Springer US 2018; Springer Nature; Springer; Springer Nature B.V
• Subjects: Aromatic compounds; Biphenyl (Compound); Chemistry; Chemistry and Materials Science; Chemistry, Organic; Dioxides; Infrared spectroscopy; NMR; NMR spectroscopy; Nuclear magnetic resonance; Nuclear magnetic resonance spectroscopy; Organic Chemistry; Organic sulfur compounds; Pharmacy; Physical Sciences; Science & Technology; Spectrum analysis; Structural analysis; Synthesis; bicyclic compounds; hydroxylamine; isoxazolidines; nitrosulfodienes; heterocyclization; sulfolanes; nucleophilic addition
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-018-2233-y

A method was developed based on reactions of 2-benzylidene-3-methyl-4-nitro-3-thiolene 1,1-dioxide and its substituted analogs with hydroxylamine and N -methylhydroxylamine for the synthesis of 3-aryl-6а-methyl-6-nitrohexahydrothieno[2,3- d ]isoxazole 4,4-dioxides – new representatives of original bicyclic structures combining condensed isoxazolidine and sulfolane rings. The structures of the obtained compounds were established by methods of IR spectroscopy, one-dimensional 1 Н and 13 С NMR spectroscopy, two-dimensional 1 Н– 13 С HMQC and 1 Н– 13 С HMBC experiments, and X-ray structural analysis.