doi:10.12202/j.0476-0301.2020159范威^{1, 2,,}
1.滁州城市职业学院科研处，239000，安徽滁州
2.南京大学化学化工学院，210023，江苏南京
基金项目:安徽省教育厅科研重点资助项目（KJ2020A1252）;滁州城市职业学院“质粒抽提创新团队”资助项目

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通讯作者:范威（1988—），男，讲师，博士。研究方向：有机合成。 e-mail：fanweipujing@126.com

中图分类号:O626

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收稿日期:2020-05-03
网络出版日期:2020-09-08
刊出日期:2020-08-25

The [2 + 2 + 1] synthesis of 2,3,5-trisubstituted thiophenes

Wei FAN^{1, 2,,}
1. Office of Research Affairs, Chuzhou City Vocation College, 239000, Chuzhou, Anhui, China
2. College of Chemistry and Chemical Engineering, Nanjing University, 210023, Nanjing, Jiangsu, China



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摘要
摘要:噻吩骨架存在于替诺立定、西他生坦、莫他匹酮等生物碱中，可用作抗炎药、降压药、PDE3抑制剂. 对该骨架的修饰，一直是有机合成的热点. 在碱促进下，1,4-二羰衍生物和硫氰基芳酮经[2 + 2 + 1]反应，构建了噻吩骨架，同时实现了C-2位和C-5位的双芳酰基化、C-3位的芳基化. 分别从红外、核磁、质谱和单晶不同角度证实了产物的结构. 该反应机制涉及[3 + 2]环加成、原位开环、互变异构、S_N2反应等过程.
关键词:[2 + 2 + 1]反应/
噻吩骨架/
双芳酰基化/
芳基化
Abstract:Thiophene skeleton is present in alkaloids tinoridine, sitaxentan and motapizone, used as anti-inflammatory drugs, anti-hypertensive drugs, and PDE3 inhibitors. Modifications of this skeleton are highly desired. Under the promotion of alkali, 1,4-dicarbonyls and thiocyanato aryl ketone could undergo [2 + 2 + 1] reaction to construct thiophene skeleton. Simultaneously, bisaroylation at C-2 and C-5 positions and arylation at C-3 position were realized. Infrared, nuclear magnetic, mass spectrometry and single crystal all confirmed structure of the product. The reaction should involve [3 + 2] cycloaddition, in situ ring opening, tautomerization, S_N2 reaction and other processes.
Key words:[2 + 2 + 1] reaction/
thiophene skeleton/
diaroylation/
arylation