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, Dattatray Dhawale, B. V Subba Reddy, S. M J Zaidi, Salems Al-Deyab, V. V. Balasubramanian, T. Mori, A. Vinu

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6 Citations (Scopus)

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
Pages (from-to)2237-2240
Number of pages4
JournalSynlett
Volume23
Issue number15
DOIs
Publication statusPublished - 2012
Externally publishedYes

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Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chauhan, S., Mane, G. P., Anand, C., Dhawale, D., Reddy, B. V. S., Zaidi, S. M. J., Al-Deyab, S., Balasubramanian, V. V., Mori, T., & Vinu, A. (2012). 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. Synlett, 23(15), 2237-2240. https://doi.org/10.1055/s-0031-1290452