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Communication | Regular issue | Vol 68, No. 6, 2006, pp.1105-1108
Published online, 28th April, 2006
DOI: 10.3987/COM-06-10741
Synthesis and Fluorescence of 6-(4-Dimethylaminophenyl)- and 6-[2-(4-N,N-Disubstituted Aminophenyl)vinyl]-4-methylthio-2-oxo-2H-pyran-3-carbonitriles in Solution and in the Solid States

Naoko Mizuyama, Yuka Murakami, Junko Nagaoka, Shinya Kohra, Kazuo Ueda, Kyoko Hiraoka, Yasuhiro Shigemitsu, and Yoshinori Tominaga*

*Faculty of Enviromental Studies of Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Fluorescent dyes, 6-(4-dimethylaminophenyl)-4-methylthio- and 6-[2-(4-N,N- disubstituted aminophenyl)vinyl]-4-methylthio-2-oxo-2H-pyran-3-carbonitriles (3a-d) were synthesized by the reaction of 4-dimethylaminoacetophenone (1a) and 4-aminobenzalacetone derivatives (1b-d) with ketene dithioacetal (2) in the presence of sodium hydroxide in dimethyl- sulfoxide at room temperature. These 2-pyrone derivatives (3a-d) showed orange and red fluoresecence (Fmax: 607, 699, 705, 645 nm) in dichloromethane solution. The preparation and fluorescence 4-amino-2H-pyrone derivatives is also described.