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Synthesis 2006(24): 4187-4199  
DOI: 10.1055/s-2006-950365
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Xiang-Shan Wang*a,b,c, Mei-Mei Zhanga, Hong Jiangc, Da-Qing Shia,c, Shu-Jiang Tua,c, Xian-Yong Weib, Zhi-Min Zongb
a Department of Chemistry, Xuzhou Normal University, Xuzhou Jiangsu, 221116, P. R. of China
b School of Chemical Engineering, China University of Mining and Technology, Xuzhou Jiangsu 221008, P. R. of China
c The Key Laboratory of Biotechnology for Medical Plant of Jiangsu Province, Xuzhou Jiangsu 221116, P. R. of China
Fax: +86(516)83403164; e-Mail: xswang1974@yahoo.com;
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Publication History

Received 6 July 2006
Publication Date:
13 November 2006 (online)

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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.

Key words

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

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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) Å3, 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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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) Å3, 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.

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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) Å3, 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.