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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 4
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Original Articles

Formation of Chromenes and Coumarin Derivatives From Salicylaldehydes and 2-Pentenedioate: Facile Route to 3-Formylcoumarins

Seetharamaiyer Padmanabhan Department of Biochemical Pharmacology, School of Pharmacy, State University of New York at Buffalo, Buffalo, NY, 14260, USA
,
Ravikumar Peri Department of Biochemical Pharmacology, School of Pharmacy, State University of New York at Buffalo, Buffalo, NY, 14260, USA
&
David J. Triggle Department of Biochemical Pharmacology, School of Pharmacy, State University of New York at Buffalo, Buffalo, NY, 14260, USA
Pages 827-831 | Received 19 Jul 1995, Published online: 21 Nov 2007
 
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Abstract

Condensation of salicylaldehydes with diethyl 2-pentenedioate under the Knoevenagel conditions afforded either coumarin-3-acrylates or 2H-chromenedicarboxylate derivatives depending on the substituents on the aryl nucleus. Osmium tetroxide catalyzed periodate oxidation of coumarin-3-acrylates gave 3-formylcoumarin derivatives.

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