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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 21
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Original Articles

Tungstophosphoric Acid–Catalyzed Imino-Diels–Alder Reaction: An Efficient One-Pot Synthesis of Pyrano- and Furanoquinoline Derivatives

, , &
Pages 3825-3832 | Received 01 Dec 2008, Published online: 07 Oct 2009
 

Abstract

Tungstophosphoric acid has been found to be an efficient catalyst for the synthesis of pyranos- and furanoquinolines through the Imino-Diels–Alder reaction involving one-pot coupling of benzaldehydes, anilines, and 3,4-dihydro-2 H-pyran or 2,3-dihydrofuran. The products are formed at room temperature in excellent yields in a short period of time.

ACKNOWLEDGMENTS

The authors thank the Council of Scientific and Industrial Research and the University Grants Commission, New Delhi for financial assistance.

Notes

a The reaction of benzaldehyde, aniline, and 3,4-dyhydro-2H-pyran was conducted using different amounts of PTA in MeCN at room temperature.

a The ratio of 4 and 5 was determined by 1H NMR spectra of the crude products, and their structures were determined from the spectra (1H NMR and MS) and analytical data of the pure compounds.

Part 176 in the series “Studies on novel synthetic methodologies.”

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