Synthesis and characterization of some novel polyfunctionally substituted indeno[2,1-b]thiophene compounds derived from indanones

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• 作者：Tzu Liang Fu ; Ing Jing Wang
• 关键词：Indandione ; Indanone ; Indeno[2 ; 1-b]thiophene ; Gewald reaction
• 刊名：Dyes and Pigments
• 出版年：2008
• 出版时间：2008
• 年：2008
• 卷：76
• 期：3
• 页码：590-595
• 全文大小：181 K

文摘

Condensation of 3-dicyanovinylindan-1-one rong>3rong> with arylamines rong>5arong>–rong>5crong> afforded 2-[3-(substituted-amino)-inden-1-ylidene]-malononitriles rong>7arong>–rong>7crong>, which were converted to 2-amino-indeno[2,1-b]thiophene rong>8arong>–rong>8crong> using the Gewald reaction. Cyclization of ethyl(1-indanylidene)-cyanoacetate rong>4rong> with elemental sulfur gave 2-amino-8H-indeno[2,1-b]thiophene-3-carboxylic acid ethyl ester rong>9rong>. Acetylation of rong>9rong> with acetic anhydride afforded the 2-acetyl compound rong>11rong>, which was condensed with arylaldehydes rong>12arong>–rong>12crong> to yield the corresponding 2-amino-indeno[2,1-b]thiophene moiety rong>13arong>–rong>13crong> containing a methine chromophore located at the 8-position using the Knoevenagel reaction. Compound rong>9rong> was condensed with N,N-dimethylaminobenzaldehyde rong>12drong> in piperidine to afford the corresponding 2-amino-indeno[2,1-b]thiophene compound rong>13drong>. Electronic absorption spectra of these compounds were discussed.