Abstract <p>A novel solid-state ionic liquid catalyst, 4-sulfo-2,3,4,5,6,7,8,9-octahydroimidazo[1,2-<i>a</i>]azepin-4-ium chloride (DBUST-Cl), was synthesized from readily available reagents under mild conditions. A green, one-pot, multicomponent procedure for the preparation of polyhydroquinoline derivatives was developed using DBUST-Cl. The condensation of aromatic aldehydes, ethyl acetoacetate, 5,5-dimethylcyclohexane-1,3-dione, and ammonium acetate in ethanol at ambient temperature (25–35°C) proceeded to completion within 2 h, affording the products in 72–97% yield. The structures of DBUST-Cl and the synthesized polyhydroquinolines were confirmed by FTIR, <sup>1</sup>H and <sup>13</sup>C NMR, and ESI-MS spectroscopic analyses.</p>

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Rapid and Environmentally Benign Synthesis of Polyhydroquinolines Using DBUST-Cl as a New Solid-Phase Catalyst

  • B. A. Shelke,
  • B. U. Sonwane,
  • A. A. Pund,
  • P. Deshpande,
  • M. G. Shioorkar,
  • B. Magre,
  • S. R. Vaidya

摘要

Abstract

A novel solid-state ionic liquid catalyst, 4-sulfo-2,3,4,5,6,7,8,9-octahydroimidazo[1,2-a]azepin-4-ium chloride (DBUST-Cl), was synthesized from readily available reagents under mild conditions. A green, one-pot, multicomponent procedure for the preparation of polyhydroquinoline derivatives was developed using DBUST-Cl. The condensation of aromatic aldehydes, ethyl acetoacetate, 5,5-dimethylcyclohexane-1,3-dione, and ammonium acetate in ethanol at ambient temperature (25–35°C) proceeded to completion within 2 h, affording the products in 72–97% yield. The structures of DBUST-Cl and the synthesized polyhydroquinolines were confirmed by FTIR, 1H and 13C NMR, and ESI-MS spectroscopic analyses.