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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 3
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Original Articles

Polyphosphoric Acid–Mediated, One-Pot, Novel Reactions to Build Polymethoxyarylnaphthalene Lignans

, , , , , , & show all
Pages 351-360 | Received 05 Jan 2009, Published online: 06 Jan 2010
 

Abstract

The one-pot reaction of succinic anhydride with 1,2-dimethoxybenzene furnished two structurally complicated polymethoxyarylnaphthalene lignans, polymethoxyarylnaphthol 1 as the minor product and polymethoxynaphtho[1,2-b]oxacycloheptatrienone 2 as the major product, in the presence of a small amount of polyphosphoric acid (PPA) as catalyst at 140°C and yielded 2 as a single product in good yield when a large amount of PPA as solvent was employed at 60–80°C. The novel structures of 1 and 2 were elucidated from 1H NMR, 13C NMR, infrared (IR), and Electrospray ionization–mass spectrometry (ESI-MS) and further confirmed by x-ray diffractions. The possible mechanisms for the formation of 1 and 2 were also proposed.

ACKNOWLEDGMENT

The authors are very grateful to Professor Jiong Jia of Shandong University for recording of part of the NMR spectra, collecting x-ray diffraction data of one of the two crystals (2), and discussing the work.

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