Pentadienone compound containing quinazolinone aryloxy as well as preparation method and application thereof

[0065] Example 1, (1E,4E)-3-((2-(3-oxo-5-phenyl-1,4-pentadien-1-yl)phenoxy)methyl)quinazoline- 4-(3 H )-Kone (A1) Synthesis

[0066] (1) quinazoline-4-(3 H )-ketone synthesis

[0067] Add 27.5 g (0.2 mol) of anthranilic acid and 36.1 g (0.8 mol) of formamide into a 250 mL three-necked flask equipped with a thermometer and a condenser tube to keep the temperature at 135-150 ° C. During this process, the system changes from light gray to The turbid liquid turned into a yellowish-brown clear liquid, and the reaction was tracked by TLC. The reaction was complete in about 5 hours. After cooling down to 100°C naturally, 100 mL of water was slowly added to the system to decompose excess formamide, and a light gray solid was precipitated at the same time. After natural cooling, it was transferred to a large beaker, and a large amount of water was added to still precipitate off-white solids. Suction filtration and drying gave 28.88 g of the product. Recrystallization with absolu...

[0078] Embodiment 2, the synthesis of compound (A2)

[0079] Steps (1)-(4) are the same as the steps (1)-(4) of Embodiment 1;

[0080] The difference between step (5) and step (5) of Example 1 is: add 0.78 g (5.56 mmol) p-chlorobenzaldehyde instead of 0.58 g (5.5 mmol) benzaldehyde, and react for 10 hours to obtain 1.23 g yellow solid, melting point ° C, yield Rate 86.5%;

[0081] The difference between step (6) and Example 1 step (6) is: add 0.37 g (1.31mmol) 1-(4-chlorophenyl)-5-(2-hydroxyphenyl)-1,4-pentadiene -3-one, instead of 0.33 g (1.31 mmol) 1-(2-hydroxyphenyl)-1,4-pentadien-3-one, reacted for 8 hours, recrystallized to obtain 0.23 g white solid, melting point 195-197°C , yield 39.6%.

[0082] Embodiment 3, the synthesis of compound (A3)

[0083] Step (1)-(4) is the same as embodiment 1 (1)-(4);

[0084] Step (5) is the same as embodiment 1 (5) method and condition. The difference is that 0.68 g (5.49 mmol) of 1-(2-fluorophenyl)-5-(2-hydroxyphenyl)-1,4-pentadien-3-one was added and reacted for 10 hours to obtain 1.10 g of a yellow solid, Yield 82.1%.

[0085] Step (6) is the same as embodiment 1 (6) method and condition. The difference is that 0.35 g (1.31 mmol) 1-(2-fluorophenyl)-5-(2-hydroxyphenyl)-1,4-pentadien-3-one was added, reacted for 5 hours, and recrystallized to obtain 0.25 g yellow Solid, melting point 142-144°C, yield 44.7%.