Pyridine/Potassium tert-Butoxide Catalyzed Benzannulation
of β-Diketones with Dimethyl Acetylenedicarboxylate

Bin Hu; Ling-Guo Meng; Yan-Ling Liu; Mao Liang; Song Xue

doi:10.1055/s-0029-1217035

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Synthesis 2009(24): 4137-4141
DOI: 10.1055/s-0029-1217035

PAPER

Pyridine/Potassium tert-Butoxide Catalyzed Benzannulation of β-Diketones with Dimethyl Acetylenedicarboxylate

Bin Hu, Ling-Guo Meng, Yan-Ling Liu, Mao Liang, Song Xue*
Department of Applied Chemistry, Tianjin University of Technology, Tianjin 300384, P. R. of China
Fax: +86(22)60214250; e-Mail: xuesong@ustc.edu.cn;

Further Information

Publication History

Received 23 July 2009
Publication Date:
12 October 2009 (online)

Abstract
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Abstract

A benzannulation reaction of β-diketones with dimethyl acetylenedicarboxylate catalyzed by pyridine and potassium tert-butoxide is described. Fully substituted benzenes are synthesized from simple and commercially available starting materials under mild conditions in high yields.

Key words

benzannulation - dimethyl acetylenedicarboxylate - pyridine - β-diketones - potassium tert-butoxide

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13

X-ray data of 5c have been deposited at CCDC as deposition number CCDC 727040. Empirical Formula: C₂₃H₂₂O₉; Formula Weight: 442.41; Crystal color, Habit: colorless, prismatic; Crystal Dimensions: 0.12 × 0.10 × 0.08 mm; Crystal System: monoclinic; Lattice Type: primitive; Lattice Parameters: a = 13.259 (3) Å, b = 6.2983 (13)Å, c = 26.596 (5) Å, β = 98.07 (3)˚, V = 2199.0(8) Å^³; Space group: P2 (1)/c; Z value = 4; Dcalc = 1.336 g/cm^³; F000 = 928; Residuals: R, Rw: 0.0597, 0.1465.