A Mild, Convenient and Efficient Single-Step Method for the Synthesis of Polysubstituted Furans via Ammonium Ylide Routes

Mingjin Fan; Lina Guo; Xueyuan Liu; Weimin Liu; Yongmin Liang

doi:10.1055/s-2004-834944

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Synthesis 2005(3): 391-396
DOI: 10.1055/s-2004-834944

PAPER

A Mild, Convenient and Efficient Single-Step Method for the Synthesis of Polysubstituted Furans via Ammonium Ylide Routes

Mingjin Fan^a, Lina Guo^a, Xueyuan Liu^a, Weimin Liu^b, Yongmin Liang*^a,b
^a National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
^b Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China
Fax: +86(931)8912582; e-Mail: liangym1@hotmail.com;

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Publication History

Received 14 September 2004
Publication Date:
08 December 2004 (online)

Abstract
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Abstract

A new and convenient cyclization method for the synthesis of polysubstituted furans in a single-step via ammonium ylide routes was reported. In this process, dimethyl acetylenedicarboxylate reacted with ammonium ylide to produce polysubstituted furan in the presence of anhydrous K₂CO₃ at room temperature. It is very economical, environmentally friendly and very easy to carry out.

Key words

substituted furans - ammonium ylide - cyclization

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8

Crystal data for 3a: CCDC 249973. C₁₄H₁₂O₅, mp: 68-70 °C; chemical formula weight: 260.24, monoclinic space group P2 (1)/c, a = 14.698 (2), b = 11.720 (1), c = 7.3105 (7) Å; α = 90.00°, β = 97.92 (9)°, γ = 90.00°, U = 1247.3 (2) Å³. T = 290 (2) K, Z = 4, D_C = 1.386 Mg/M³, µ = 0.106 mm^-1, λ = 0.71073 Å, F(000) 544, Crystal size 0.52 × 0.48 × 0.48 mm³, 2255 independent reflections [R(int) = 0.0122], Reflections collected 2690: Refinement method, full-matrix least-squares on F²: Goodness-of-fit on F² 1.073: Final R indices [I > 2δ (I)] R1 = 0.0383, wR2 = 0.1038, R indices (all data) R1 = 0.0524, wR2 = 0.0138. Extinction coefficient 0.126 (7), Largest diff. peak and hole 0.173 Å^-3 and -0.163e Å^-3.