Ethyl 2,4-dioxoalkanoates as starting materials for a convenient route to 3(2H) furanones and 3(2H) furanimines |
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| Affiliation: | 1. Dipartimento di Scienze Farmaceutiche, UK;2. Dipartimento Chimico, Università di Ferrara UK;1. NEUROFARBA, Sezione di Farmaceutica e Nutraceutica, Università degli Studi di Firenze, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Firenze, Italy;2. Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK;3. NEUROFARBA, Sezione di Farmacologia e Tossicologia, Università degli Studi di Firenze, Viale Pieraccini 6, 50139 Firenze, Italy;1. Institute of Chemical Physics, Vilnius University, Sauletekio Av. 3, LT-10257 Vilnius, Lithuania;2. Institute of Chemistry, Vilnius University, Naugarduko Str. 24, LT-03225 Vilnius, Lithuania;1. Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology, PO Box 131, Cheongryang, Seoul 130-650, Republic of Korea;2. Department of Chemistry, Yonsei University, Seodaemun-gu, Seoul 120-749, Republic of Korea;3. Biological Chemistry, Korea University of Science and Technology, Yuseong-Gu, Daejon 305-350, Republic of Korea;4. Department of Chemistry, Inha University, Nam-gu, Incheon 402-751, Republic of Korea;5. Department of Global Medical Science, Sungshin University, Seoul 142-732, Republic of Korea;1. Department of Chemistry, University of the West Indies, St. Augustine, Trinidad and Tobago;2. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK;3. Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/A, Parma 43124, Italy;4. Dipartimento di Scienze del Farmaco, Sezione Chimica, Università di Catania, Viale Andrea Doria, 6, 95125 Catania, Italy |
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| Abstract: | Addition of both Grignard reagents or hydride reducing agents to the ester group of the readily available 2,4-dioxoalkanoates, while the 1,3-diketone fragment is suitably masked both in form of an isoxazole ring or as an enaminone function, allows a useful preparation of a variety of α'-hydroxy-1, 3-diketone moieties. Acid-promoted cyclodehydration of these compounds leads to 3(2H) furanones or 3(2H) furanimines depending on the substitution pattern and on reaction conditions. |
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