HFO‐1234yf as a CF 3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones
| Autor: | Thomas G. F. Marsh, Alessia Santambrogio, Ben J. Murray, Lee T. Boulton, Juan A. Aguilar, Dmitry S. Yufit, Graham Sandford, William D. G. Brittain |
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| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | European Journal of Organic Chemistry, 2023, Vol.26(11), pp.e202300058 [Peer Reviewed Journal] |
| ISSN: | 1099-0690 1434-193X |
| DOI: | 10.1002/ejoc.202300058 |
| Popis: | Trifluoromethyl ynones derived from the refrigerant gas HFO-1234yf (2,3,3,3-tetrafluoropropene) react with nucleophiles via a Michael-type addition process and the allenolate intermediate formed reacts intramolecularly with a carbonyl group to form heterocyclic derivatives. Thus, reaction of 2-amino and 2-hydroxyl benzaldehyde or ketone substrates with trifluoromethyl ynone derivatives gives trifluoromethyl quinoline and chromene products by a one-pot tandem ring closing sequence, forming pharmaceutically relevant structures from an inexpensive starting material without the need for transition metals or column chromatography. The 2-trifluoromethylquinoline products also show unusual fluxional behaviour, which was explored through 2-D NMR and X-ray crystallographic studies. |
| Databáze: | OpenAIRE |
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