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Synthesis 2008(12): 1902-1910  
DOI: 10.1055/s-2008-1067087
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient and Highly Selective Method for the Synthesis of 3-Arylbenzo­quinoline Derivatives Catalyzed by Iodine via Three-Component Reactions

Xiang-Shan Wang*a,b, Qing Lia, Jian-Rong Wua, Yu-Ling Lia, Chang-Sheng Yaoa, Shu-Jiang Tua,b
a School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China
b The Key Laboratory of Biotechnology, Medical Plant, Xuzhou, Jiangsu 221116, P. R. of China
Fax: +86(516)83500065; e-Mail: xswang1974@yahoo.com;
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Publication History

Received 12 February 2008
Publication Date:
16 May 2008 (online)

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Abstract

A mild, efficient and highly selective method for the synthesis of benzo[f]quinoline derivatives via three-component reactions of arylaldehydes, naphthalen-2-amine and ketones or β-keto esters using iodine as catalyst is described. It should be noted that only one product was obtained, with high selectivity, when ketones or β-keto esters with two different α-hydrogen atoms were chosen as reactants.

Key words

benzo[f]quinoline - iodine - ketone - β-keto ester - synthesis

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X-ray crystal data for 4c. Empirical formula: C22H18BrN; Formula weight: 376.28; Colorless block crystals; Crystal size: 0.46 × 0.45 × 0.17 mm; Crystal system: triclinic; Space group: P1; Unit cell dimensions: a = 9.203 (2) Å, b = 10.173 (2) Å, c = 10.582 (2) Å, α = 97.868 (3)°, β = 107.038 (3)°, γ = 112.235 (3)°; V = 841.7 (3) Å3; Z = 2; D(calcd) = 1.485 g/cm3; F(000) = 384, µ(MoKα) = 2.444 mm-1. Intensity data were collected on a Rigaku Mercury diffractometer with graphite monochromated MoKα radiation (λ = 0.71070 Å) using ω scan mode with 3.09° < θ < 25.35°. Unique reflections collected 3062; 2625 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 gave R = 0.0374 and wR = 0.0877.