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SYNTHESIS OF BICYCLIC SYSTEMS CONTAINING FUSED SULFOLANE AND ISOXAZOLIDINE RINGS

Ирина Евгеньевна Ефремова, Анна Валерьевна Серебрянникова, Лидия Викторовна Лапшина, Валентина Михайловна Берестовицкая, Владислав Владимирович Гуржий
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Abstract


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 1Н and 13С NMR spectroscopy, two-dimensional 1Н–13С HMQC and 1Н–13С HMBC experiments, and X-ray structural analysis.

Keywords


bicyclic compounds, hydroxylamine, isoxazolidines, nitrosulfodienes, sulfolanes, heterocyclization, nucleophilic addition.

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