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Synthesis, characterization, and photophysical properties of some new thieno[2,3-b]pyridines bearing phenylethenyl moiety
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-10-28 , DOI: 10.1002/jhet.4391 Ahmed F. M. EL-Mahdy 1 , Etify A. Bakhite 1 , Shams H. Abdel-Hafez 2 , Omaima F. Ibrahim 1 , Hajjaj H. M. Abdu-Allah 3 , Islam S. Marae 1
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-10-28 , DOI: 10.1002/jhet.4391 Ahmed F. M. EL-Mahdy 1 , Etify A. Bakhite 1 , Shams H. Abdel-Hafez 2 , Omaima F. Ibrahim 1 , Hajjaj H. M. Abdu-Allah 3 , Islam S. Marae 1
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5-Acetyl-3-cyano-6-methyl-4-(2-phenylethenyl)pyridine-2(1H)-thione (2) was synthesized by interaction of cinnamylidene-2-cyanothioacetamide 1 and acetylacetone or via one-pot reaction of E-cinnamaldehyde, 2-cyanothioacetamide, and acetylacetone. Reaction of 2 with ethyl iodide (3a) or N-chloroacetyl derivative of aromatic amines 3b–e in boiling ethanol containing sodium ethoxide gave the corresponding thioether 4a and 5-acetyl-3-amino-2-(N-arylcarbamoyl)-6-methyl-4-(2-phenylethenyl)thieno[2,3-b]pyridines 5b–e, respectively. Compound 5e was reacted with 2,5-dimethoxytetrahydrofuran or triethyl orthoformate to furnish pyrrolylthienopyyridine 6 or pyrdiothienopyrimidinone 7, respectively. The photophysical properties of 5b, 5c, 5e, and 7 were fully studied and the obtained results included herein. The fluorescence data confirmed that compounds 5b, 5c, 5e, and 7 exhibit aggregation-induced emission behavior with high absolute quantum yields.
中文翻译：
一些新的带有苯基乙烯基的噻吩并[2,3-b]吡啶的合成、表征和光物理性质
5-Acetyl-3-cyano-6-methyl-4-(2-phenylethenyl)pyridine-2(1 H )-thione ( 2 ) 由cinnamylidene-2-cyanothioacetamide 1与乙酰丙酮相互作用或一锅法合成E-肉桂醛、2-氰基硫代乙酰胺和乙酰丙酮。2与碘乙烷 ( 3a ) 或芳香胺3b-e的N-氯乙酰衍生物在含有乙醇钠的沸腾乙醇中反应，得到相应的硫醚4a和5-乙酰基-3-氨基-2-( N-芳基氨基甲酰基)-6-甲基-4-(2-苯基乙烯)噻吩并[2,3 - b ]吡啶5b-e， 分别。化合物5e与2，5-二甲氧基四氢呋喃或原甲酸三乙酯反应分别得到吡咯基噻吩并嘧啶6或吡二噻吩并嘧啶酮7。对5b、5c、5e和7的光物理性质进行了充分研究，所得结果包括在本文中。荧光数据证实化合物5b、5c、5e和7表现出具有高绝对量子产率的聚集诱导发射行为。
更新日期：2021-10-28
中文翻译：
一些新的带有苯基乙烯基的噻吩并[2,3-b]吡啶的合成、表征和光物理性质
5-Acetyl-3-cyano-6-methyl-4-(2-phenylethenyl)pyridine-2(1 H )-thione ( 2 ) 由cinnamylidene-2-cyanothioacetamide 1与乙酰丙酮相互作用或一锅法合成E-肉桂醛、2-氰基硫代乙酰胺和乙酰丙酮。2与碘乙烷 ( 3a ) 或芳香胺3b-e的N-氯乙酰衍生物在含有乙醇钠的沸腾乙醇中反应，得到相应的硫醚4a和5-乙酰基-3-氨基-2-( N-芳基氨基甲酰基)-6-甲基-4-(2-苯基乙烯)噻吩并[2,3 - b ]吡啶5b-e， 分别。化合物5e与2，5-二甲氧基四氢呋喃或原甲酸三乙酯反应分别得到吡咯基噻吩并嘧啶6或吡二噻吩并嘧啶酮7。对5b、5c、5e和7的光物理性质进行了充分研究，所得结果包括在本文中。荧光数据证实化合物5b、5c、5e和7表现出具有高绝对量子产率的聚集诱导发射行为。
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