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

Chauhan, S., Mane, G. P., Anand, C., Dhawale, D. S., Reddy, B. V. Subba, Zaidi, S. M. J., Al-Deyab, Salem S., Balasubramanian, V. V., Mori, T. and 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. doi:10.1055/s-0031-1290452


Author Chauhan, S.
Mane, G. P.
Anand, C.
Dhawale, D. S.
Reddy, B. V. Subba
Zaidi, S. M. J.
Al-Deyab, Salem S.
Balasubramanian, V. V.
Mori, T.
Vinu, A.
Title 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
Journal name Synlett   Check publisher's open access policy
ISSN 0936-5214
1437-2096
Publication date 2012-09-01
Sub-type Article (original research)
DOI 10.1055/s-0031-1290452
Volume 23
Issue 15
Start page 2237
End page 2240
Total pages 4
Place of publication Stuttgart, Germany
Publisher Georg Thieme
Language eng
Formatted 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 Brønsted 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.
Keyword Nanoporous catalysts
Enol ethers
Aryl amines
Imino-Diels-Alder reaction
Tetrahydroquinolines
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Australian Institute for Bioengineering and Nanotechnology Publications
 
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