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To 5.00 g (16.1 MMOL) of 1, 3-BIS-A-NAPHTHY-2-PROPEN-1-ONE (1) in 25 ml water free ethanol 1.89 G (8.11 MMOL) biphenylbenzamidine hydrochlorid are added. A solution of 1.07 G (19. 08 MMOL) potassium hydroxide in 25 ml water free ethanol is added during 15 min. Dry air was bubbled through the reaction mixture. The reaction mixture is REFLUXED for 24 h. The reaction mixture is poured into water. The solid is filtered off and is washed with water. The product is crystallized 2 times from acetic acid (96-98 %). Melting point: 226-230 C.
To 6.60 g (20.1 mmol) of 1 ,3-bis-(2,4-dimethoxy-phenyl)-2-propen-1 -one (1) in 40 ml water free ethanol 2.34 g (10.1 mmol) biphnenyl-benzamidine hydrochloride are added under argon. A solution of 1.41 g (25.1 mmol) potassium hydroxide (85%) in 40 ml water freeethanol is added during 15 mm. Dry air is bubbled through the reaction mixture. The reaction mixture is refluxed for 48 h and then poured into water. The water phase is extracted with dichloromethane. The organic phase is dried with MgSO and the solvent is removed in vacuum. A column chromatography on silica gel with toluene/hexane 3/2 give the desired product J-2 (melting point: 165 167 C).
With N-ethyl-N,N-diisopropylamine; In ethanol; ethyl acetate; for 30h;Reflux;
Third step: Synthesis of 2-([1,1'-biphenyl]-4-yl)-4,8-diphenyl-1,4,5,6-tetrahydropyrimido[4,5-f]quinazoline (5). All manipulations were carried out in air, without any further purification of commercial solvents/chemicals. 6-benzylidene-2-phenyl-7,8-dihydroquinazolin-5(6H)-one (6.25 g) and benzamidine hydrochloride (3.8 g) were allowed to stir in a mixture of ethanol (30 mL) and ethyl acetate (50 mL). A solution of N-ethyl-N-isopropylpropan-2-amine (5 mL) in 20 mL ethanol is then added within 10 min via an addition. After the addition, the suspension was refluxed for 30 h. After 30 minutes the suspension turned into a solution. After 30 hours, the solution is cooled down, and a yellow precipitate appears. Work Up11 ml of acetic acid is then slowly added to the suspension and stirred for 30 minutes at room temperature. The precipitate is filtered using a Buechner and washed with 20 mL ethanol and dried overnight in a vacuum oven.Yield: 6.05 g (73%).
With copper diacetate; sodium carbonate; In toluene; at 110℃; for 30h;
Add to a 100ml three-necked flaskM-bromobenzaldehyde (10.8mmol, 2g),P-phenylbenzamide hydrochloride(21.6mmol, 3.8g),Na2CO3 (21.6 mmol, 2.2 g),Cu(OAc) 2 (1.08 mmol, 0.22 g),The molar ratio is 1:2: 2: 0.1 feeding, solvent selection of 50 g of toluene, reaction control at 110 C for 30 h, filtered, washed with water, recrystallized from absolute ethanol Filtration, the obtained cake was dried in vacuo to give the product 4.97 g, yield 85%.
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