| 99% |
With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; for 24h; Schlenk technique; |
|
| 99% |
With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; for 24h; |
12 5 mol% of {L2Eu [N (SiMe3) 2] · THF} 2 and 5 mol% ofDBU catalyzes the reaction of 2-amino-4,5-dimethoxybenzonitrile with carbon dioxide at 100 ° C under atmospheric pressure to prepare 2,4-quinazolinediones
In anhydrous, anaerobic, argon protection,0.0999 g (7.5 x 10-5 mol) of {L2Eu [N (SiMe3) 2] THF} 2 was added to the reaction flask,An additional 11.2 μL (7.5 × 10 -5 mol) DBU was added, under the protection of carbon dioxide bag,Add 2 mL of dimethyl sulfoxide, add 0.3333 g (1.5 x 10-3 mol) of 2-amino-4,5-dimethoxybenzonitrile,The reaction was stirred in a constant temperature bath at 100 ° C. After 24 hours,Add 5mL 2mol / L hydrochloric acid quenching reaction, suction filtration, successively with 3 × 5mL hydrochloric acid,Toluene and diethyl ether to remove the residual solvent, drying the solid to obtain the product,The yield is 99%. |
| 98% |
With tetrabutylammonium tungstate In dimethyl sulfoxide at 119.84℃; for 48h; Autoclave; |
|
| 98% |
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 110℃; for 24h; Autoclave; |
4.4. Synthesis of quinazoline-2,4(1H,3H)-diones 5 from 2-aminobenzonitriles 4 and CO2: general procedure
General procedure: Table 5: To a DMSO-d6 solution (1 mL) of 2-aminobenzonitrile 4a (1 mmol) in a stainless steel autoclave was added a catalyst (0.01 mmol) under an argon atmosphere. The autoclave was sealed, heated at 110°C and then pressurized with CO2 of 2 MPa. The cyclization reaction of 4a proceeded by the magnetic stirring of the resulting mixture at 110°C for 3 h. After the reaction the autoclave was cooled in an ice bath and depressurized. The chemical yield of quinazoline-2,4(1H,3H)-dione 5a was determined by integrating 1HNMR with reference to an internal standard (3,5-dimethoxybenzylalcohol), which was added to the reaction mixture. Table 6: DMSO solution (6 mL) of 4 (6 mmol) was treated for the carboxylative cyclization of 4 with CO2 according to the procedure of Table 5. After the reaction, the autoclave was cooled in an ice bath and depressurized, and the reaction mixture was added to water (60 mL). The precipitation was collected by filtration, washed with water and diethyl ether, and then dried in vacuo at 35°C for 15 h to give the pure product 5. |
| 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 80℃; for 4h; |
|
| 97% |
With bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere; |
|
| 97% |
With Zhabuye basic salt-lake brine at 140℃; for 7h; Sealed tube; |
|
| 96% |
With C3H6O3*C9H16N2 In neat (no solvent) at 40℃; for 24h; Green chemistry; |
|
| 95% |
With 3-butyl-1-methylimidazolium acetate at 90℃; for 10h; Green chemistry; |
|
| 95% |
With [P4444][2-MIm] at 79.84℃; for 10h; |
|
| 95% |
With triethylamine; zinc(II) iodide In toluene at 30℃; for 21h; |
|
| 94% |
With cholin hydroxide In water for 0.333333h; |
|
| 94% |
With 2,4,6-triamino-s-triazine In water at 120℃; for 18h; High pressure; |
|
| 93% |
With water at 160℃; for 18h; Autoclave; Green chemistry; |
|
| 93% |
Stage #1: 2-amino-4,5-dimethoxybenzonitrile With 2,2'-iminobis[ethanol] In water for 0.0333333h; Autoclave;
Stage #2: carbon dioxide In water at 100℃; for 12h; Autoclave; |
7
0.89 g (5 mmol) of 2-amino-4,5-dimethoxybenzonitrile was placed in a polytetrafluoroethyleneliner of astainless steel reactorand 3 mL of a 0.5 mol / L aqueous solution of diethanolamine was added, After 2 minutes of mixing, carbon dioxide was introducedand the temperature was raised to 100 ° C. The carbon dioxide pressure was adjusted to 1 MPa for the carboxylation reaction under stable conditions, and the reaction time was 12hours.After completion of the reaction, the reaction system was cooled to room temperature slowly released unreacted carbon dioxide, was added 10mL of deionized waterand stirred dispersion product, resulting precipitate was filtered and washed with a small amount of distilled water, then washed with 15mL / times with methyl tert-butyl ether threetimes And the product 6,7-dimethoxyquinazolin-2,4- (1H, 3H) -dione was dried at a temperature of 100 ° C in a yield of 93% |
| 93% |
With water; 2,2'-iminobis[ethanol] at 100℃; for 12h; |
|
| 92% |
With 1,8-diazabicyclo[5.4.0]-7-undecenium trifluoroethanolate at 29.84℃; for 24h; |
|
| 92% |
With 14.6 wtpercent amine functionalized MCM-41 In water at 130℃; for 18h; Green chemistry; |
|
| 92% |
With [HDBN][2-PyOH] In dimethyl sulfoxide at 60℃; for 6h; Autoclave; |
16
General procedure: Weigh 0.160g (1.35mmol) of o-aminobenzonitrile, add it to a stainless steel autoclave with a PTFE liner and a volume of 10ml, and then add 3ml of DMSO solvent.And 0.297g (1.35mmol) of proton-type ionic liquid [HDBN][2-PyOH] was added dropwise as a reaction catalyst; then the autoclave was sealed, and CO2 gas was blown in for 10 minutes,Ensure that the air in the kettle is fully exhausted, and then adjust the pressure reducing valve to 0.3MPa,The autoclave was placed in a constant temperature water bath at 60°C and stirred for reaction. After 4h reaction,Slowly exhaust the gas in the kettle, add 0.228g (1.35mmol) after the reaction kettle is cooled to room temperature3,5-Dimethoxybenzyl alcohol was used as an internal standard, and then a certain amount of deionized water was added to it,The precipitate was separated by centrifugation, washed with tert-butyl methyl ether, and dried under vacuum for 10 hours.Prepare quinazoline-2,4(1H,3H)-dione,The structure of the reaction product was determined by NMR spectroscopy and the reaction yield was calculated by NMR internal standard method. |
| 91.3% |
With C9H17N2(1+)*C13H19O(1-) In dimethyl sulfoxide at 120℃; for 20h; Autoclave; |
9; 13 Example 9:
The aminobenzonitrile compound (14) (1 mol), organic salt catalyst (0.05 mmol) and 1 ml of DMSOAdd to an autoclave with mechanical stirring and temperature-controlled heating device. Seal the reaction kettle, replace the air in the kettle with CO2 3 times, thenFill the reaction kettle with CO 2 to an initial pressure of 0.1 MPa, increase the temperature to 120 °C, and react for 20 hours. After the reaction is complete, use iceThe water mixture cooled the reaction kettle to 0°C, released residual gas, added 10ml of dichloromethane to precipitate the product, and removed the precipitated product from DCMSeparate from the solution, then add 10ml of tetrahydrofuran (THF) to centrifuge to clean the precipitated product three times, and vacuum dry to obtain the product(20) The product is white powder, and the isolated yield of the product is 91.30%. After the separated DCM solution was vacuum dried for 6hThe DCM is removed, the catalyst is recovered, and the obtained catalyst can be used directly. |
| 90% |
With C7H14N3(1+)*C3HF6O(1-) at 35℃; for 12h; Green chemistry; |
|
| 88% |
With N,N,N',N'-tetramethylguanidine at 120℃; for 4h; Autoclave; |
|
| 87% |
With tetra-butylphosphonium arginine In neat (no solvent) at 100℃; for 12h; Green chemistry; |
|
| 82% |
With C3N3O3(3-) In dimethyl sulfoxide at 100℃; for 24h; |
|
|
With lanthanum magnesia mixed oxide In water at 140℃; for 14h; |
|
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