Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides |
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| Institution: | 1. Centre for Semiochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;3. Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India;1. Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy;2. Dipartimento di Medicina Molecolare, Università degli Studi di Padova, Via Gabelli 63, 35121 Padova, Italy;3. Department of Biochemistry and Molecular Biology, University of Southern Denmark, Odense, Denmark;4. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Padova, Via Marzolo 5, 35131 Padova, Italy;1. Laboratory of Medicinal and Advanced Synthetic Chemistry (Lab MASC), Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, Perugia I-06123, Italy;2. Laboratory of Bioinorganic Chemistry, University of Florence, Via della Lastruccia 3, Sesto Fiorentino (Firenze) I-50019, Italy;3. Neurofarba Dept., Section of Pharmaceutical and Nutriceutical Sciences, University of Florence, Via U. Schiff 6, Sesto Fiorentino (Firenze) I-50019, Italy;1. School of Food and Biological Engineering, Hefei University of Technology, Hefei 230009, China;2. Department of Chemistry, University of Science and Technology of China, Hefei 230026, China;1. Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy;2. Centro Interdipartimentale di Ricerca in Oncologia Clinica e Dipartimento Biomedico di Medicina Interna e Specialistica, Sezione di Malattie Infettive, Università degli Studi di Palermo, Via del Vespro 129, 90127 Palermo, Italy;3. Sezione di Gastroenterologia, Dipartimento di Biomedicina Interna e Specialistica, Università degli Studi di Palermo, Via del Vespro 129, 90127 Palermo, Italy |
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| Abstract: | α-Sulfonamidation of β-ketoesters with sulfonyl azide has been developed for the first time using a catalytic amount of Ru(II) complex to produce the 1-oxo-2-(sulfonamido)-2,3-dihydro-1H-indene-2-carboxylate and 1-oxo-2-(sulfonamido)-1,2,3,4-tetrahydronaphthalene-2-carboxylate derivatives in good yields. This method also works well with α-iodotetralones to afford the N-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulphonamide derivatives under similar conditions. |
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| Keywords: | Transition metal catalysis Cyclic β-ketoesters Sulfonyl azides α-Sulfonamidation |
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