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

Abstract

Abstract: 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 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) 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.

Key words: 2,2’-Diphenyl-1,4-benzoxazin-3(4H)-one, Microwave synthesis, Crystal structure

CLC Number:

O626

TrendMD:

WEI Wen-Ping¹, ZHANG Dan-Feng¹, ZHAO Ping¹, YUAN Qiao-Long¹, HUANG Bao-Tong^1,2
. Synthesis and Crystal Structure Characterization of 2,2'-Diphenyl-1,4-benzoxazin-3(4H)-one under Microwave Irradiation[J]. Chem. J. Chinese Universities, doi: .

References

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