A series of fluorinated propargylamines have been synthesized from the one-pot three-component reaction of fluorobenzaldehyde, aniline and phenylacetylene under solvent-free and microwave ...irradiation. The fluorinated propargylamines were then further transformed to chalcones or quinoline derivatives respectively depending on the different structures of propargylamines.
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► A one-pot solvent-free microwave irradiation reaction was investigated. ► A series of fluorinated propargylamines have been synthesized. ► The products were further transformed to chalcones or quinolines. ► The possible mechanism was proposed.
A series of fluorinated propargylamines have been synthesized from the one-pot three-component reaction of fluorobenzaldehyde, aniline and phenylacetylene under solvent-free and microwave irradiation. The fluorinated propargylamines were then further transformed to chalcones or quinoline derivatives respectively depending on the different structures of propargylamines.
Variously substituted 1,3-thiazines have been prepared by a three-component reaction involving a thioamide, an aldehyde, and an alkene. Two diastereomeric thiazines were transformed by ...stereoselective Staudinger reaction into the corresponding chloro-β-lactam-condensed-1,3-thiazines, and one of them was rearranged in basic media to afford a highly substituted 1,4-thiazepine. Several of the obtained compounds (six 1,3-thiazines and one β-lactam-condensed-1,3-thiazine) were analyzed by X-ray crystallography, which enabled to assign their spatial arrangement and stereochemistry.
1,1′-Butylenebis(3-methyl-3
H
-imidazol-1-ium) dihydrogensulfate as an efficient, halogen-free and reusable binuclear Brönsted ionic liquid catalyzed the synthesis of pyrano4,3-
b
pyran derivatives ...at 60 °C under solvent-free conditions. This method has the advantages of high yield, clean reactions, simple methodology and short reaction time. The ionic liquid could be recycled without significant loss of activity. The structure of the compounds was confirmed by IR,
1
H NMR,
13
C NMR, mass and elemental analysis.
Graphical abstract
A three-component reaction of aldehyde, (
E
)-3-aminobut-2-enenitrile and dimedone in ionic liquids, gave 1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-4-arylquinoline-3-carbonitrile derivatives at ...50 °C. Using 2-hydroxynaphthalene-1,4-dione to replace dimedone at the same reaction conditions resulted in another series of polysubstituted benzo
h
quinoline derivatives in high yields. This method involves the advantages of mild conditions, high yields, one-pot synthesis, and an environmentally benign procedure.
Graphical abstract
The zwitterions generated from phenanthiridine and dialkyl acetylenedicarboxylates (DAADs) react with a variety of arylidenemalononitriles, affording substituted pyrido1,2-fphenanthridines.
A series of N-phenyl and N-pyridyl-aminomethylenebisphosphonates substituted in their aromatic rings with fluorine atoms or trifluoromethyl groups have been synthesized by a three component approach. ...They were screened for potential antiosteoporetic activity using mouse macrophage-like J774E cells. Most of the compounds appeared to be moderate inhibitors of macrophage cells proliferation compared to known the antiosteoporetic drug, Incandronate. Their potency was compared with their structural analogues, hydroxymethylene-bisphosphonate 2 and ethylidenebisphosphonates 3, which appeared to be equipotent. Although the aminomethylenebisphosphonates 1 show low stability in aqueous solutions, the most stable, i.e., N-(3-trifluoromethylphenyl)-aminomethylenebisphosphonic acid, was chosen for in vivo testing on sheep with induced osteoporosis. This compound had marginal influence on the bone structure recovery.
A three-component reaction of 2-alkynylbenzaldoxime, carbodiimide, and bromine provides a novel and efficient approach to functionalized 1-aminoisoquinolines. This unexpected reaction proceeds ...through electrophilic cyclization, 3+2 cycloaddition, rearrangement and hydrolyzation.
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The functionalized spiroindoline-3,40-pyrano3,2-hquinolines were efficiently prepared in high yields from three-component reaction of 8-hydroxyquinoline, isatins and malononitrile or ethyl ...cyanoacetate in ethanol at room temperature for about 12 h in the presence of piperidine.
A one-pot three-component cascade reaction for the green synthesis of a new class of 2-amino-5,8-dihydro-3H-pyrido2,3-dpyrimidin-4-ones was developed from the condensation of aromatic aldehydes with ...2,6-diaminopyrimidin-4(3H)-one and acetophenone derivatives or various cyclic ketones in the presence of a catalytic amount of sodium carbonate in a mixture of water and ethanol at 60
∘
C
. This reaction led to the construction of two carbon–carbon bonds and one carbon–nitrogen bond in a single synthetic step.
Trichloroisocyanuric acid was found to be a highly efficient homogeneous catalyst for synthesis of imidazoles via one-pot, three-component condensation of aldehydes with benzil and ammonium acetate. ...The valuable advantages of this method are high yields of products, easy work-up and purification procedure, and use of a commercially available, inexpensive, and non-volatile catalyst.
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