l-Proline catalyzed intermolecular cyclization of methyl perfluoroalk-2-ynoates with salicylaldehyde: Synthesis of perfluoroalkylated 2H-chromenes

Yan, Xufeng; Shen, Dandan; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo

doi:10.1016/j.jfluchem.2016.06.004

Cited by 6 publications

(1 citation statement)

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“…Similarly, no product could be recovered from reaction of 1 with 2‐hydroxyacetophenone, side reactions in this case occurring due to the presence of enolisable protons. Syntheses of 2‐hydroxy‐2‐trifluoromethyl chromene derivatives have been accomplished previously by the reaction of salicylaldehyde substrates with CF 3 ‐ynoates, [14] CF 3 ‐alkenyl triflates, [15] and CF 3 ‐alkynyl phosphonates [16] but all required amine catalysts at reflux temperatures and/or long reaction times. This is in stark contrast to the relatively mild and rapid conditions utilised here.…”

Section: Resultsmentioning

confidence: 99%

HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

et al. 2023

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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 2hydroxyl 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.

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Section: Resultsmentioning

confidence: 99%

HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

et al. 2023

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Room‐Temperature Cascade Electrophilic Addition/Cyclization/Oxidation Reactions: Divergent Selective Synthesis of Brominated 2H‐Chromenes, 2H‐Chromen‐2‐ols and 2H‐Chromen‐2‐ones

Shen,

Li,

Zhao

et al. 2024

Chemistry A European J

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The room temperature metal‐free cascade electrophilic addition/cyclization/oxidation reactions of (3‐phenoxyprop‐1‐yn‐1‐yl)benzenes to divergently synthesize various brominated benzopyran derivatives (3‐bromo‐2H‐chromenes, 3‐bromo‐2H‐chromen‐2‐ols and 3‐bromo coumarins) by tuning the amount of Br2 and H2O have been developed. The method exhibited high selectivity, mild reaction conditions, broad substrate scope, high efficiency, and the applicability for derivatization of the brominated products. The importance of the strategies provides a great advantage for selective synthesis of brominated benzopyran derivatives.

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ChemInform Abstract: L‐Proline Catalyzed Intermolecular Cyclization of Methyl Perfluoroalk‐2‐ynoates with Salicylaldehyde: Synthesis of Perfluoroalkylated 2H‐Chromenes.

et al. 2016

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l-Proline catalyzed intermolecular cyclization of methyl perfluoroalk-2-ynoates with salicylaldehyde: Synthesis of perfluoroalkylated 2H-chromenes

Cited by 6 publications

References 47 publications

HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

Room‐Temperature Cascade Electrophilic Addition/Cyclization/Oxidation Reactions: Divergent Selective Synthesis of Brominated 2H‐Chromenes, 2H‐Chromen‐2‐ols and 2H‐Chromen‐2‐ones

ChemInform Abstract: L‐Proline Catalyzed Intermolecular Cyclization of Methyl Perfluoroalk‐2‐ynoates with Salicylaldehyde: Synthesis of Perfluoroalkylated 2H‐Chromenes.

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l-Proline catalyzed intermolecular cyclization of methyl perfluoroalk-2-ynoates with salicylaldehyde: Synthesis of perfluoroalkylated 2H-chromenes

Cited by 6 publications

References 47 publications

HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

Room‐Temperature Cascade Electrophilic Addition/Cyclization/Oxidation Reactions: Divergent Selective Synthesis of Brominated 2H‐Chromenes, 2H‐Chromen‐2‐ols and 2H‐Chromen‐2‐ones

ChemInform Abstract: L‐Proline Catalyzed Intermolecular Cyclization of Methyl Perfluoroalk‐2‐ynoates with Salicylaldehyde: Synthesis of Perfluoroalkylated 2H‐Chromenes.

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HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones