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Reaction of 6-aryl- or styryl-4-methylsulfanyl-2-oxo-2H-pyrans with active methylene compounds and fluorescence properties of the products
✍ Scribed by Naoko Mizuyama; Yuka Murakami; Takatoshi Nakatani; Keiko Kuronita; Shinya Kohra; Kazuo Ueda; Kyoko Hiraoka; Yoshinori Tominaga
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2008
- Tongue
- English
- Weight
- 922 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
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New 2‐pyrone derivatives, dialkyl 3‐cyano‐6‐phenyl‐2‐oxo‐2__H__‐pyran‐4‐ylmalonates and alkyl 3‐cyano‐6‐phenyl‐2‐oxo‐2__H__‐pyran‐4‐ylacetates, which were easily prepared by the reaction of 6‐aryl‐4‐methyl‐sulfanyl‐2‐oxo‐2__H__‐pyran‐3‐carbonitriles with active methylene compounds in the presence of potassium carbonate, show fluorescence emission radiation. The light‐emitting region of dimethyl 3‐cyano‐6‐(4‐N,N‐dimethylamino)styryl‐2‐oxo‐2__H__‐pyran‐4‐ylmalonate (7h) was 620 nm in dichloromethane, making this compound a typical red fluorescent compound. Methyl 8‐hydroxy‐6‐methyl‐1‐oxo‐3‐phenyl‐1__H__‐pyrano‐[3,4‐c]pyridine‐5‐carboxylate deriv‐atives also showed fluorescence in the solid state. This is the first example of fluorescence in fused 2‐pyrone derivatives.
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