* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 110℃; for 24 h; Autoclave
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.
94%
With fibrous nanosilica functionalized with sodium tripolyphosphate and 3-aminopropyltriethoxysilane In neat (no solvent) at 70℃; for 0.833333 h; Autoclave; Green chemistry
General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70°C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials.
93%
Stage #1: With 2,2'-iminobis[ethanol] In water for 0.0333333 h; Autoclave Stage #2: at 100℃; for 12 h; Autoclave
Weigh 0.763 g (5 mmol) of 2-amino-5-chlorobenzonitrile was placed in a polytetrafluoroethylene liner of a stainless steel reactor, and3 mL of a diethanolamine aqueous solution having a concentration of 1.33 mol / L was added and stirred for 2 minutes , The carbon dioxide was heated and the temperature was raisedto 100 ° C, and the carbon dioxide pressure was adjusted to 1 MPa for the carboxylation reaction under stable conditions for 12 hours.Antiupon end, the reaction system was cooled to room temperature slowly released unreacted carbon dioxide, was added 10mL of deionized water and stirreddispersion product, resulting precipitate was filtered and washed with a small amount of distilled water, and then 15mL / wash three times with methyl tert-butyl ether Andthe product was dried at a temperature of 100 ° C to give 6-chloroquinazoline-2,4 (1H, 3H) -dione having a yield of 93percent.
92%
at 70℃; for 1 h; Autoclave
General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70°C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.
91%
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 24 h;
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 0.2949 g (1.5 × 10 -3 mol) of 2-amino-5-chlorobenzonitrile,The reaction was stirred in a constant temperature bath at 100 ° C. After 24h, add 5mL 2mol / L hydrochloric acid to quench the reaction,Suction filtration, successively washed with 3 × 5mL hydrochloric acid, toluene and ether solids, the residual solvent was stripped, dried solids,The product was obtained in 91percent yield.
Reference：
[1] Heteroatom Chemistry, 2012, vol. 23, # 3, p. 276 - 280
[2] RSC Advances, 2015, vol. 5, # 7, p. 5032 - 5037
[3] Tetrahedron, 2018, vol. 74, # 24, p. 2914 - 2920
[4] Green Chemistry, 2014, vol. 16, # 6, p. 3142 - 3148
[5] ChemSusChem, 2018, vol. 11, # 24, p. 4219 - 4225
[6] Tetrahedron, 2002, vol. 58, # 16, p. 3155 - 3158
[7] Synthesis, 2007, # 16, p. 2524 - 2528
[8] Tetrahedron Letters, 2004, vol. 45, # 38, p. 7073 - 7075
[9] Angewandte Chemie - International Edition, 2012, vol. 51, # 27, p. 6700 - 6703
[10] RSC Advances, 2015, vol. 5, # 20, p. 15668 - 15673
[11] Tetrahedron, 2010, vol. 66, # 23, p. 4063 - 4067
[12] Inorganic Chemistry, 2012, vol. 51, # 23, p. 13001 - 13008
[13] Catalysis Science and Technology, 2016, vol. 6, # 5, p. 1435 - 1441
[14] Phosphorus, Sulfur and Silicon and the Related Elements, 2018, vol. 193, # 8, p. 535 - 544
[15] Patent: CN106946800, 2017, A, . Location in patent: Paragraph 0022-0023
[16] Angewandte Chemie - International Edition, 2014, vol. 53, # 23, p. 5922 - 5925[17] Angew. Chem., 2014, vol. 53-126, # 23, p. 6032 - 6035
[18] Catalysis Communications, 2015, vol. 72, p. 91 - 96
[19] Chemistry - An Asian Journal, 2016, vol. 11, # 19, p. 2735 - 2740
[20] Green Chemistry, 2014, vol. 16, # 1, p. 221 - 225
[21] RSC Advances, 2014, vol. 4, # 92, p. 50993 - 50997
[22] European Journal of Organic Chemistry, 2016, vol. 2016, # 14, p. 2555 - 2559
[23] Patent: CN105153048, 2017, B, . Location in patent: Paragraph 0126; 0127
[24] Canadian Journal of Chemistry, 2019, vol. 97, # 3, p. 212 - 218
[25] RSC Advances, 2015, vol. 5, # 31, p. 24670 - 24674
[26] Green Chemistry, 2013, vol. 15, # 6, p. 1485 - 1489
[27] Catalysis Science and Technology, 2014, vol. 4, # 6, p. 1608 - 1614
[28] ChemCatChem, 2016, vol. 8, # 1, p. 244 - 250
[29] ChemSusChem, 2017, vol. 10, # 6, p. 1145 - 1151
[30] RSC Advances, 2016, vol. 6, # 112, p. 111079 - 111089
2
[ 57-13-6 ]
[ 635-21-2 ]
[ 1640-60-4 ]
Yield
Reaction Conditions
Operation in experiment
94%
at 200℃; for 3 h;
Step 1 6-Chloroquinazoline-2,4(1H,3H)-dione A 250 mL round bottom flask was charged with 2-amino-5-chlorobenzoic acid (17.2 g, 0.1 mol) and urea (30 g, 0.5 mol). The resulting mixture was heated to 200° C. for 3 h. Work up: the reaction mixture was washed by water and filtered. The solid was dried to give 18.5 g (94percent) of the product. MS m/z: 196 (M+H+).
94%
at 200℃; for 3 h;
A 250 mL round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17.2 g, 0.1 mol) and urea (30 g, 0.5 mol). The resulting mixture was heated to 200 °C for 3 h. Work up: the reaction mixture was washed by water and filtered. The solid was dried to give 18.5 g (94percent) of the product. MS m/z: 196 (M+H+)
79%
at 150℃; for 10 h;
General procedure: A mixture of 2-aminobenzoic acid 3a (2.00 g, 14.91 mmol), urea (4.40 g,73.26 mmol) in phenol (6.00 g, 63.76 mmol) was heated at 150 Cunder the reflux for 10 h. The reaction mixture was cooled downto 100 C and ethanol/water (1:1) 10 mL was added drop-wise.The reaction mixture was cooled to rt, filtered, washed with ethanol(5 mL), and dried to afford 4a in 53percent yield (1.26 g).
Reference：
[1] Patent: US2010/120741, 2010, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2011/112731, 2011, A2, . Location in patent: Page/Page column 79
[3] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 6, p. 2390 - 2400
[6] Tetrahedron, 2012, vol. 68, # 43, p. 8908 - 8915
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[8] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80
3
[ 5202-85-7 ]
[ 1640-60-4 ]
Yield
Reaction Conditions
Operation in experiment
76%
With hydrogenchloride; urea In pyridine; water
Part B: The preparation of 6-chloro-2,4-quinazoline-dione. Urea (2.64 g) and 5-chloro-2-amino benzamide (3.75 g) were dissolved in 100 mL of pyridine. To this solution was added 10percent HCl (aq.) (6 drops) and the resulting solution was refluxed for 12-18 hours. The reaction mixture was evaporated to dryness and the resulting residue was suspended in 125 mL of water. The pH of the suspension was adjusted to 6 with dilute hydrochloric acid and the solid was recovered by filtration. The filter cake was washed well with water and was dried to yield 3.27 g of buff powder (76percent): 1 H NMR (DMSO-d6, 300 MHz) δ11.45 (s, 1H), 11.25 (s, 1H), 7.81 (d, 1H), 7.66 (dd, 1H), 7.18 (d, 1H).
Reference：
[1] Patent: US5187168, 1993, A,
4
[ 917-61-3 ]
[ 635-21-2 ]
[ 1640-60-4 ]
Yield
Reaction Conditions
Operation in experiment
44%
Stage #1: With acetic acid In water at 30℃; for 0.5 h; Stage #2: With sodium hydroxide In water at 30℃; Stage #3: With hydrogenchloride In water
Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-ammo-5-chlorobenzoic acid (10 g, 58 48 mmol, 1 00 equiv) in water (100 mL), acetic acid (8 g, 133 33 mmol, 2 24 equiv) This was followed by the addition of NaOCN (8 2 g, 126 15 mmol, 2 13 equiv) The mixture was stirred for 30 rains at 3O0C To this was added sodium hydroxide (86 g, 2 15 mol, 37 00 equiv) The resulting solution was stirred overnight at 30cC The solids were collected by filtration The residue was dissolved in water The pH value of the solution was adjusted to 7 with hydrogen chloπde (12 mol/L) The solids were collected by filtration This resulted in 5 g (44percent) of 6 chloroqmnazolme-2,4(lH,3H)-dione as a white solid.
Reference：
[1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 431 - 433
[3] Journal of Chemical Research, 2007, # 6, p. 358 - 361
6
[ 635-21-2 ]
[ 1640-60-4 ]
Reference：
[1] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 940
[3] Patent: US5688803, 1997, A,
7
[ 5922-60-1 ]
[ 68-12-2 ]
[ 1640-60-4 ]
Reference：
[1] Organic Process Research and Development, 2016, vol. 20, # 12, p. 2067 - 2073
Reference：
[1] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 940
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 940
12
[ 20028-68-6 ]
[ 1640-60-4 ]
Reference：
[1] Scientia Sinica (English Edition), 1958, vol. 7, p. 617,628[2] Chem.Abstr., 1958, p. 15539
[3] Huaxue Xuebao, 1957, vol. 23, p. 391,396, 397[4] Chem.Abstr., 1958, p. 15539
13
[ 5202-89-1 ]
[ 1640-60-4 ]
Reference：
[1] Journal of the Chemical Society, 1948, p. 1759,1765
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