Reaction of some antiinflammatory 17 beta-(2-aminooxazol-4-yl) steroids with hydrogen peroxide. Synthesis of steroid-17-spiro-5'-oxazolidine-2',4'-diones |
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| Authors: | G Rapi M Ginanneschi M Chelli S Chimichi |
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| Affiliation: | Cattedra di Chimica e Propedeutica Biochimica, Facoltà di Medicina e Chirurgia and Centro C.N.R. per lo Studio della Chimica e della Struttura dei Composti Eterociclici e loro Applicazioni, c/o Dipartimento di Chimica Organica, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Italy |
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| Abstract: | The heterocyclic moiety of 17 beta-(2-aminooxazol-4-yl) steroids is sensitive to the oxidizing action of hydrogen peroxide and yields products mainly from the opening of the amino-oxazole ring. Unlike simple 2-aminooxazoles, it does not rearrange to 2-imidazolone and the expected steroidal hydroperoxyimidazolidinones were not detected. Among the substances we isolated, N-(aminocarbonyl)-17 alpha-hydroxy-17-carboxamides (2a) and (3a) undergo spontaneous cyclization, in the reaction conditions, giving steroid-17-spirooxazolidinediones (2d) and (3d). Spirane (2d) was synthesized in high yields from (2a) in strongly alkaline medium. |
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| Keywords: | Please address correspondence to: Prof. Gianfranco Rapi Istituto di Chimica Organica della Università Via Gino Capponi 9 I-50121 Firenze Italy. |
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