A Facile, Simple and Convenient Method for the Synthesis of 14-Alkyl or Aryl-14-H-Dibenzo[a,j]xanthenes Catalyzed by pTSA in Solution and Solvent-Free Conditions

Abstract

An efficient and straightforward procedure for the synthesis of 14-alkyl or aryl-14-H-dibenzo[a,j]xanthenes has been achieved through the one-pot condensation of β-naphthol with alkyl or aryl aldehydes in the presence of p-toluene sulfonic acid as catalyst under two conditions: organic solvent and solvent-free media.

xanthene - one-pot reaction - condensation - aldehyde - β-naphthol - p-toluenesulfonic acid - solvent-free - organic solvent

References

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Selected Characterization Data of:14-(3-Nitrophenyl)-14- H -dibenzo[ a , j ]xanthene (Table 2, Entry 7): yellow solid; mp 211 °C. IR (KBr): 3040, 1612, 1584, 1516, 1248, 812, 803 cm^-1. ¹H NMR (200 MHz, CDCl₃): δ = 6.65 (s, 1 H), 7.15-8.6 (m, 17 H). ¹³C NMR (50 MHz, CDCl₃): δ = 38.1, 116.3, 118.5, 122.1, 122.4, 123.1, 125.0, 127.7, 129.5, 129.9, 130, 131.5, 131.8, 134.7, 147.4, 148.6, 149.2. Anal. Calcd for C₂₇H₁₇NO₃: C, 80.38; H, 4.25; N, 3.47. Found: C, 80.27; H, 4.08; N, 3.56.
14-(4-Methoxyphenyl) -14- H -dibenzo[ a , j ]xanthene (Table 2, Entry 11): yellow solid; mp 204 °C. IR (KBr): 3040, 2912, 1616, 1580, 1248, 823, 806 cm^-1. ¹H NMR (200 MHz, CDCl₃): δ = 3.67 (s, 3 H), 6.52 (s, 1 H), 6.71 (d, J = 9.5 Hz, 2 H), 7.38-7.95 (m, 14 H), 8.43 (d, J = 9.5 Hz, 2 H). ¹³C NMR (50 MHz, CDCl₃): δ = 37.5, 53.9, 114.3, 117.9, 118.4, 123.1, 124.6, 127.2, 129.1, 129.2, 131.5, 133.7, 137.8, 149.1, 158.3. Anal. Calcd for C₂₈H₂₀O₂: C, 86.57; H, 5.19. Found: C, 86.32; H, 5.31.