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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 5
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Original Articles

Synthesis of Novel Indeno[1,2-c]isoquinoline Derivatives

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Pages 666-676 | Received 31 Mar 2009, Published online: 04 Feb 2010
 

Abstract

Indeno[1,2-c]isochromene was prepared using the readily obtainable starting materials via the condensation of dimethyl homophthalate with 3,4-dimethoxybenzaldehyde in the presence of sodium methoxide in absolute methanol followed by saponification and cyclization with concentrated sulfuric acid at 0°C. The proclivity of cyclized product for undergoing nucleophilic addition has been tested by reaction with nitrogen nucleophiles. Structural assignments are based on spectroscopic data (infrared, 1H NMR, 13C NMR, and mass spectra) and confirmed by the single-crystal x-ray molecular structure (2 and 3).

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