| 90% |
With guanidineacetic acid at 100℃; for 1h; |
|
| 88% |
In toluene at 110℃; Inert atmosphere; |
|
| 88% |
In toluene at 110℃; |
|
| 88% |
In toluene at 110℃; |
|
| 88% |
In toluene at 110℃; Inert atmosphere; |
|
| 88% |
In toluene at 110℃; |
|
| 76% |
In ethanol for 6h; Reflux; |
The acetophenone (25 mmol) was solved in ethanol (20 mL) and N,N-dimethylformamide dimethyl acetal (37 mmol) was added. The reaction mixture was stirred under reflux for 6 h and concentrated. The residue was elutriated in hexane and the remaining precipitate was filtered off, washed several times with hexane and dried.Intermediate B1: (E)-3-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one Yield: 76%1H-NMR (300 MHz, d6-DMSO): α=7.92 (m, 2H), 7.67 (d, 1H), 7.20 (m, 2H), 5.77 (d, 1H), 3.10 (bs, 3H), 2.87 (br s, 3H) ppm. |
| 70% |
With boron trifluoride diethyl ether complex In toluene at 110℃; for 24h; |
|
|
for 14h; Heating; |
|
|
In N,N-dimethyl-formamide |
|
|
at 120℃; for 16h; |
|
|
In 5,5-dimethyl-1,3-cyclohexadiene Reflux; |
General procedure for synthesis of substituted (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one 2 (a-u)
General procedure: To the appropriate methyl ketones 1 (a-u) (0.01 mol) in round-bottom flask, DMF-DMA (N,N-Dimethylformamide dimethyl acetal) was added and refluxed in xylene for the appropriate time. The solvent was evaporated in vacuum and the residual solid was crystallized from ethanol to afford corresponding pure product 2. |
|
at 110℃; for 0.166667h; Microwave irradiation; |
1 Synthesis of 1-(4-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one (3)
To a solution of p-fluoroacetophenone (1) (10 mmol) in xylene or without solvent was added dimethylformamide-dimethylacetal (DMF-DMA) (12 mmol) and the mixture was mixed in a HP-500 Plus process vessel. The vessel was capped properly and irradiated by microwaves under pressurized conditions (17.2 bar, 110 °C) for 10 min. The excess DMF-DMA was evaporated in vacuo and the residue was dissolved in ether (50 mL) and dried over MgSO4. After evaporation of the solvent the resulting solid was recrystallized from hexane to afford (E)-1-(4-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one (2), The physical and spectral data of the synthesized compound are listed below. Mp.: 64-65 °C; IR (KBr) cm-1: 1664 (C=O), 1598 (C=N); 1H NMR (CDCl3): δ 3.02 (s, 6H, N(CH3)2), 5.67 (d, 1H, J = 12.3 Hz, -CO-CH]), 7.10 (d, 2H, Ar-H), 7.80 (d, J = 12.3 Hz, 1H, =CH-N), 7.92 (d, 2H, Ar-H).; MS (m/z): 193 (M+); C11H12FNO:Anal. Calcd: C, 68.38; H, 6.26; N, 7.25. Found C, 68.28; H, 6.16; N, 7.35. %. |
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In toluene at 110℃; Inert atmosphere; |
|
|
In toluene at 110℃; |
|
|
for 2h; Reflux; |
41
A mixture of 1-(4-fluorophenyl)ethanone (2 g) and 1,1-dimethoxy-N,N-dimethylmethanamine (4 ml) was refluxed for 2 h. The solvent was removed. To the residue was added hexane to give the title compound as crystals (889 mg).1H-NMR (300 MHz, DMSO-d6) δ: 2.92 (3H, s), 3.14 (3H, s), 5.82 (1H, d, J=12.2 Hz), 7.24 (2H, m), 7.71 (1H, d, J=12.2 Hz), 7.96 (2H, dd, J=8.9, 5.7 Hz). |
|
In 5,5-dimethyl-1,3-cyclohexadiene for 7h; Reflux; |
(1) Preparation of N,N-dimethylenaminones
General procedure: The N,N-dimethylenaminones were synthesized according to literature method with slight modifications. 1 To a solution of ketones (1.54 g, 12.8 mmol) in xylene (15 mL) was added N,N-dimethylformamide dimethylacetal (3.6 mL, 25.7 mmol) and refluxed for 7 h (monitored by TLC). Xylene was then removed by distillation and crude residue was purified by column chromatography (silica gel; hexane-EtOAc = 3:7) to yield (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one ( 1 ) as a pure light yellow solid. |
|
In acetonitrile at 82℃; for 1h; Microwave irradiation; Sealed tube; |
Synthesis of compounds 7a-m
General procedure: A vial containing a mixture of aromatic ketone 13a-m (1 mmol) and N,N-dimethylformamide dimethyl acetal (12) (1 mmol) in CH3CN (3 mL) was sealed and placed in a Anton Paar Microwave Synthetic Reactor. The vial was subjected to microwave irradiation, programmed at 82 oC and 150W. After a period of 30 second, the temperature reached a plauteau, 82 oC, and remained constant. After stirring reaction for 60 min, 2-hydroxy-1,4-naphthoquinone (15) (1 mmol) and glacial AcOH (0.2 mmol) were added into the vial. The reaction was stirred for a further 30 min. The vial was then cooled to room temperature. Evaporation of the solvent gave crude products 7a-m, which was purified by column chromatography using a MeOH-EtOAc-DCM eluent (1:4:5) |
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