Low-temperature synthesis of pyrano- and furo[3,2-c]quinolines via Povarov reaction using a highly ordered 3D nanoporous catalyst with a high acidity

S. Chauhan, G. P. Mane, C. Anand, D. S. Dhawale, B. V.Subba Reddy, S. M.J. Zaidi, Salems Al-Deyab, V. V. Balasubramanian, T. Mori, A. Vinu

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The imines generated in situ from aryl amines and cyclic enol ethers undergo smooth [4+2] cycloaddition with 3,4-dihydro-2H-pyran (DHP) and 2,3-dihydrofuran (DHF) using the Bronsted acid sites on the aluminosilicate wall structure of the nanoporous catalyst under mild reaction conditions to afford the corresponding pyrano- and furo[3,2-c]quinolines, respectively, in good yields with high diastereoselectivity. The high activity of the catalyst is due to its high surface area, large pore volume, and well-ordered porous structure with high acidity. In addition, the catalyst was found to be highly stable and can be reused several times without affecting the activity of the catalyst.

Original languageEnglish (US)
Pages (from-to)2237-2240
Number of pages4
JournalSynlett
Volume23
Issue number15
DOIs
StatePublished - Aug 30 2012

Keywords

  • aryl amines
  • enol ethers
  • imino-Diels-Alder reaction
  • nanoporous catalysts
  • tetrahydroquinolines

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