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HFO‐1234yf as a CF 3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones
Ist Teil von
European journal of organic chemistry, 2023-03, Vol.26 (11)
Erscheinungsjahr
2023
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Abstract
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.