An Improved and Benign Synthesis of 9,10-Diarylacridine-1,8-dione and Indenoquinoline Derivatives from 3-Anilino-5,5-dimethylcyclohex-2-enones, Benzaldehydes, and 1,3-Dicarbonyl Compounds in an Ionic Liquid Medium

Abstract

Improved and green syntheses of 9,10-diarylacridine-1,8-dione and indenoquinoline derivatives were accomplished by the reactions of 3-anilino-5,5-dimethylcyclohex-2-enones, benzaldehydes, and 1,3-dicarbonyl compounds in the ionic liquid medium [bmim⁺][BF₄ ^-]. Not only the substituted anilines containing electron-donating groups, but also those with electron-withdrawing groups all gave excellent yields. Furthermore, the interesting unsymmetrical 9,10-diarylacridine-1,8-dione moiety with different groups in the 3- and 6-positions and indenoquinoline derivatives were obtained and are reported here for the first time in the literature. The Knoevenagel condensation and Michael addition intermediates were obtained successfully. A possible mechanism of the reaction is discussed in detail.

9,10-diarylacridine-1,8-diones - indenoquinolines - ionic liquids - green chemistry

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19

Crystal structure data for 4r: C₂₉H₃₁NO₃, M = 441.55, pale yellow block crystals, 0.50 × 0.47 × 0.26 mm³, triclinic, space group P-1, a = 9.6382 (15), b = 11.5847 (15), c = 12.4722 (11) Å, α = 66.075 (9), β = 70.176 (9), γ = 85.800(13)°, V = 1194.1 (3) ų, Z = 2, D _c = 1.228 g·cm^-3, F(000) = 472, µ(Mo Kα) = 0.079 mm^-1. Intensity data were collected on a Rigaku Mercury diffractometer with graphite monochromated Mo-Kα radiation (λ = 0.71070 Å) using the ω scan mode with 3.07° < θ < 25.34°; 4332 unique reflections were measured and 3733 reflections with I > 2σ(I) were used in the refinement. The structure was solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least-squares technique refined to R = 0.0539 and wR = 0.1204.

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21

Crystal structure data for 6a: C₃₀H₃₅NO₃, M = 457.59, pale yellow block crystals, 0.20 × 0.15 × 0.10 mm³, monoclinic, space group P21/c, a = 10.2337 (13), b = 17.077 (2), c = 15.2788 (19) Å, α = 90.00, β = 106.329 (3), γ = 90.00°, V = 2562.4 (5) ų, Z = 4, D _c = 1.186 g·cm^-3, F(000) = 984, µ(Mo Kα) = 0.076 mm^-1. Intensity data were collected on a CCD area diffractometer with graphite monochromated Mo-Kα radiation (λ = 0.71073Å) using the φ and ω scan modes with 2.07° < θ < 26.00°; 4985 unique reflections were measured and 1823 reflections with I > 2σ(I) were used in the refinement. The structure was solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least-squares technique refined to R = 0.0617 and wR = 0.1201.

22

Crystal structure data for 8b: C₃₄H₃₃FN₂O₃, M = 536.62, red block crystals, 0.40 × 0.21 × 0.20 mm³, monoclinic, space group P21/n, a = 113.0147 (18), b = 9.5006 (12), c = 22.985 (3) Å, α = 90.00, β = 102.850 (3), γ = 90.00°, V = 2770.9 (6) ų, Z = 4, D _c = 1.286 g·cm^-3, F(000) = 1136, µ(Mo Kα) = 0.087 mm^-1. Intensity data were collected on a Rigaku Mercury diffractometer with graphite monochromated Mo-Kα radiation (λ = 0.71070Å) using the φ and ω scan modes with 3.03° < θ < 25.34°; 3830 unique reflections were measured and 1823 reflections with I > 2σ(I) were used in the refinement. The structure was solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least-squares technique refined to R = 0.0789 and wR = 0.1544.