Thermal condensation of indoles with trifluoroacetaldehyde |
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| Affiliation: | 1. Scuola di Scienze del Farmaco e dei Prodotti della Salute, Università di Camerino, Via S. Agostino 1, 62032 Camerino, Italy;2. Medicinal Chemistry Section, Molecular Targets and Medications Discovery Branch, National Institute on Drug Abuse – Intramural Research Program, National Institutes of Health, Baltimore, MD, 333 Cassell Drive, Baltimore, MD 21224, USA;3. Department of Chemistry & Biochemistry, College of Science and Mathematics, Rowan University 201 Mullica Hill Rd, Glassboro, NJ 08028, USA;4. Department of Biomedical & Translational Sciences, College of Science and Mathematics, Rowan University 201 Mullica Hill Rd, Glassboro, NJ 08028, USA;5. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy;6. Recordati S.p.A., Drug Discovery, Via Civitali 1, 20148 Milano, Italy;7. Dipartimento di Neuroscienze, Psicologia, Area del Farmaco e Salute del Bambino (NEUROFARBA), Sezione di Farmacologia e Tossicologia, Universita'' degli Studi di Firenze, Viale Pieraccini 6, 50139 Firenze, Italy |
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| Abstract: | The title condensations provide the corresponding (1′-hydroxy-2′,2′,2′-trifluoroethyl)indoles. Indole itself, 1-methylindole and 2-methylindole gave 3-adducts in yields of 77%, 49% and 84%, respectively. 3-Substituted indoles (3-methylindole, ethyl indole-3-acetate and indole-3-ethyl acetate) afforded 2-adducts in yields of 69%, 21% and 23%, respectively. The indole adduct eliminates water at 137°C to form a transient 3-(trifluoromethylmethylene)indolenine, which reacts rapidly with nucleophiles including indole. |
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