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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 24
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Original Articles

Alum-Catalyzed Domino Synthesis of 12-Substituted-8,9,10,12-tetrahydrobenzoxanthen-11-ones Under Solvent-Free Conditions

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Pages 3538-3551 | Received 13 May 2014, Published online: 15 Oct 2014
 

Abstract

Alum is found to catalyze efficiently the one-pot, three-component condensation of aldehydes, α/β-naphthol, and dimedone to afford various 12-substituted-8,9,10,12-tetrahydrobenzoxanthen-11-ones in excellent yields. The use of alum catalyst and the solvent-free conditions make this method simple, convenient, eco-friendly, and cost-effective.

GRAPHICAL ABSTRACT

Notes

a Reaction condition: Benzaldehyde (1.0 mmol), β-naphthol (1.0 mmol), dimedone (1.0 mmol), and alum (10 mol%, 0.1 mmol), 120 °C, N2 atmosphere, 30 min.

b As revealed by TLC.

c Isolated yield.

a General reaction conditions: Aldehyde 1 (1.0 mmol), α/β-naphthol 2 (1.0 mmol), dimedone 3 (1.0 mmol, 0.140 g), and alum (10 mol%, 0.1 mmol, 0.047 g), 120 °C, N2 atmosphere.

b All the products were characterized by their physical and spectral data.

c Isolated yields.

d Literature reference of melting point.

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

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