Synthesis and X-Ray Crystal Structure of 1- and 2-Cinnamoyaloxy Acetonaphthones

Abstract

The synthesis of titled compounds were achieved in one step using hydroxyl naphthones and substituted cinnamic acids in the presence of a catalytic amount of phosphorus oxychloride. X-ray crystal studies were undertaken for three compounds and the results are presented. Compounds 1 (C₂₂H₁₅F₃O₃) and 3 (C₂₁H₁₅BrO₃) formed a monoclinic crystals while compound 2 (C₂₂H₁₅F₃O₃) formed a triclinic crystals. The observed space group of these compounds is P2₁/c and P$\bar{1}$ respectively. The 2-substituted compounds showed identical space group and showed a perpendicular arrangements of each of the substituents to the plane of the naphthyl ring. On the contrary, the 1-substituted cinnamoyal compound showed an orthogonal arrangement to naphthyl ring but the acetyl group was almost planar relative to the naphthyl moiety. The characterization of the structures of the compounds was also accomplished using high-resolution NMR spectroscopic techniques.

Graphical Abstract

The synthesis of titled compound was achieved in one step using hydroxyl naphthones and substituted cinnamic acids in the presence of a catalytic amount of phosphorus oxychloride. X-ray crystal studies were undertaken for three compounds and the results are presented. Compounds 1 and 3 formed a monoclinic crystal while compound 2 formed a triclinic crystal. The molecular formulae of compounds are as follows: C₂₂H₁₅F₃O₃ (1 and 2) and C₂₁H₁₅BrO₃(3) . The observed space group of these compounds is P2₁/c and P1 respectively.