Lewis Acid Catalyzed One-Pot Selective Synthesis of Aminobenzofurans and N-Alkyl-2-aryl-2-(arylimino)acetamides: Product Dependence on the Nature of the Aniline

Abstract

An efficient one-pot reaction between isocyanides, anilines, and salicylaldehydes (2-hydroxybenzaldehydes) in the presence of a Lewis acid proceeds smoothly at room temperature within a short time interval to afford aminobenzofurans and N-alkyl-2-aryl-2-(arylimino)acetamide derivatives in high yields depending on the electron density of the aniline component.

multicomponent reaction - Lewis acids - substituent effects - cyclization - Schiff bases

References

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Crystal data of compound 10a : C₁₈H₁₉ClN₂O₂, FW = 330.80, monoclinic, space group P21/c, a = 12.0348 (13) Å, b = 18.050 (2) Å, c = 7.9752 (9) Å, β = 102.269 (5)˚, V = 1692.9 (3) Å^³, Z = 4, T = 296 (2) K, d _calcd = 1.298 g cm^-³, F(000) = 696. Diffraction data were measured with MoKα (λ = 0.71073 Å) radiation at 296 K using a Bruker Kappa Apex 2 CCD system. A total of 2404 unique reflections were measured (θ_max = 25.00˚). Data analyses were carried out with the Fast Fourier Transform program. The structures were solved by direct methods using the SHELXS-97^¹4 program. Refinements were carried out with a full matrix least squares method against F2 using SHELXL-97.^¹5 Non-hydrogen atoms were refined with anisotropic thermal parameters. The final R value was R1 = 0.0375 and wR2 = 0.1202 with I > 2σ(I). Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre with reference number CCDC 773605.

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