Synlett 2012; 23(15): 2237-2240
DOI: 10.1055/s-0031-1290452
letter
© Georg Thieme Verlag Stuttgart · New York

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
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
,
G. P. Mane
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
,
C. Anand
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
,
D. S. Dhawale
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
,
B. V. Subba Reddy
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
b   NIMS-IICT Materials Research Center, Indian Institute of Chemical Technology, Hyderabad 500 007, India
,
S. M. J. Zaidi
c   Department of Chemical Engineering, King Fahd University of Petroleum & Minerals, Dhahran-31261, Saudi Arabia
,
Salem S. Al-Deyab
d   Department of Chemistry, Petrochemicals Research Chair, Faculty of Science, King Saud University, P.O. Box 2455 Riyadh 11451, Saudi Arabia
,
V. V. Balasubramanian
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
,
T. Mori
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
b   NIMS-IICT Materials Research Center, Indian Institute of Chemical Technology, Hyderabad 500 007, India
,
A. Vinu*
a   National Institute for Materials Science, 1-1 Namiki, Tsukuba, 305-0044, Japan
b   NIMS-IICT Materials Research Center, Indian Institute of Chemical Technology, Hyderabad 500 007, India
e   Australian Institute for Bioengineering and Nanotechnology, The University of Queensland, Brisbane 4072, Australia, Email: a.vinu@uq.edu.au
› Author Affiliations
Further Information

Publication History

Received: 23 May 2012

Accepted after revision: 25 June 2012

Publication Date:
27 August 2012 (online)


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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.