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Reaction of 6‐aryl‐ or styryl‐4‐methylsulfanyl‐2‐oxo‐2 H ‐pyrans with active methylene compounds and fluorescence properties of the products
Author(s) -
Mizuyama Naoko,
Murakami Yuka,
Nakatani Takatoshi,
Kuronita Keiko,
Kohra Shinya,
Ueda Kazuo,
Hiraoka Kyoko,
Tominaga Yoshinori
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450133
Subject(s) - chemistry , fluorescence , methylene , pyran , aryl , potassium carbonate , dichloromethane , pyridine , medicinal chemistry , alkyl , organic chemistry , physics , quantum mechanics , solvent
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.