微波法合成2,2′-二苯-1,4-苯并噁嗪-3(4H)-酮及其结构表征

Synthesis and Crystal Structure Characterization of 2,2'-Diphenyl-1,4-benzoxazin-3(4H)-one under Microwave Irradiation

Benzoxazinone usually exists in many kinds of plants.It is applied in prepharmacy synthesis,and bioactivity studies,and has been prepared from O-aminophenol and chrol-with alkine and solvent by refluxing for a long time.In this work,2,2’-diphenyl-1,4-benzoxazin-3(4H)-one was solvent-free synthesized under microwave irradiation.The configuration and conformation of the product were determined by 1H NMR,IR,MS,elementary analysis and X-ray crystal analysis.The results of X-ray crystal analysis show that the compound crystallizes in a triclinic system,space group %P%1,cell parameter %a%=0.840 7(1)nm,%b%=0.845 1(1)nm,%c%=2.254 1(3)nm,%α%=96.111(3)°,%β%=97.196(3)°,%γ%=90.229(3)°,%V%= 1^579 6(4)nm3,%Z%=4,%D%c =1.267 Mg/m3,%F%(000)= 632.0,%μ%= 0.08 mm-1.In the compound,oxazinone ring is shown chair conformation,two benzene rings is placed in two sides of oxazinone ring distortedly.In crystal state,a centrosymmetric dimmer is formed %via% hydrogen bonds generated from amides of two near molecules.The benzene rings in a same chemical environment are paralleled by a distance of 0.260 9 nm.It displays aromatic π-π stacking interactions.

Benzoxazinone usually exists in many kinds of plants. It is applied in prepharmacy synthesis, and bioactivity studies, and has been prepared from O-aminophenol and chrol- with alkine and solvent by refluxing for a long time. In this work, 2,2＇-diphenyl-1,4-benzoxazin-3 （4H）-one was solvent-free synthesized under microwave irradiation. The configuration and conformation of the product were determined by 1^H NMR, IR, MS, elementary analysis and X-ray crystal analysis. The results of X-ray crystal analysis show that the compound crystallizes in a triclinic system, space group P1, cell parameter a = 0. 840 7 （ 1 ） nm, b = 0. 845 1 （ 1 ） nm, c =2.254 1（3） nm,α =96. 111（3）°,β=97. 196（3）°, γ =90.229（3）°, V= 1. 579 6（4） nm^3, Z = 4, De = 1. 267 Mg/m^3, F（000） = 632.0,μ = 0.08 mm^-1. In the compound, oxazinone ring is shown chair conformation, two benzene rings is placed in two sides of oxazinone ring distortedly. In crystal state, a centrosymmetric dimmer is formed via hydrogen bonds generated from amides of two near molecules. The benzene rings in a same chemical environment are paralleled by a distance of 0. 260 9 nm. It displays aromatic π-π stacking interactions.