One-pot synthesis of polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 4991-4994

  Ye, Zhenjun ^a   Xu, Renbo ^a   Shao, Xusheng ^a   Xu, Xiaoyong ^a   Li, Zhong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

4H Pyran derivatives; Fluorochloro pyridyl; Multicomponent reactions (MCRs)

Indexed keywords

BENZALDEHYDE; IONIC LIQUID; LEWIS ACID; MALONONITRILE; PIPERIDINE; PROPIONIC ACID DERIVATIVE; PYRAN DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; ONE POT SYNTHESIS; PHYSICAL CHEMISTRY; REACTION TIME;

EID: 78549258084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.065     Document Type: Article

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29. 3 as the solvent and TMS as the internal standard. Chemical shifts are reported in δ (parts per million) values. Coupling constants nJ are reported in Hz. High-resolution electron mass spectra were recorded under electron impact (70 eV) condition using a MicroMass GCT CA 055 instrument. Analytical thin-layer chromatography (TLC) was carried out on precoated plates (Silica Gel 60 F254), and spots were visualized with ultraviolet (UV) light. All chemicals or reagents were purchased from standard commercial supplies.
30. General procedure for one-pot syntheses of 6a-n: To a solution of the appropriate aldehyde (1.2 mmol) in ethanol (15 mL), malononitrile (1.2 mmol) and piperidine (0.12 mmol) were added. The mixture was stirred for 0.5-1.5 h at 35 °C. After Knoevenagel condensation was finished, (monitored by TLC), 3- (2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate was added into the reaction mixture, and warmed to reflux for 1-2 min. The solvent was removed under reduced pressure. Then, the rude product was precipitated by adding 5 mL mixture solvent (PE/EA = 3:1). After filtration and drying, the pure compound was obtained.
31. 2 (M+), 451.0494; found, 451.0518.