化工学报 ›› 2019, Vol. 70 ›› Issue (S1): 110-114.DOI: 10.11949/j.issn.0438-1157.20181418

• 催化、动力学与反应器 • 上一篇    下一篇

微波促进碳酸钾催化一锅法合成2-氨基-3氰基-4-芳基-4H-苯并色烯衍生物

曾育才(),刘小玲,梁奇峰,吕鉴泉   

  1. 嘉应学院化学与环境学院,广东 梅州 514015
  • 收稿日期:2018-11-27 修回日期:2018-12-11 出版日期:2019-03-31 发布日期:2019-03-31
  • 通讯作者: 曾育才
  • 作者简介:曾育才(1961—),男,副教授,<email>mzzyc@jyu.edu.cn</email>
  • 基金资助:
    嘉应学院自然科研基金项目(2014KJY04)

One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K2CO3 under microwave irradiation

Yucai ZENG(),Xiaoling LIU,Qifeng LIANG,Jianquan LYU   

  1. College of Chemistry and Environment, Jiaying University, Meizhou 514015, Guangdong, China
  • Received:2018-11-27 Revised:2018-12-11 Online:2019-03-31 Published:2019-03-31
  • Contact: Yucai ZENG

摘要:

微波辐射下,乙醇溶剂中K2CO3催化芳甲醛、丙二腈和α-萘酚(或β-萘酚)三组分一锅法快速合成了一系列2-氨基-3-氰基-4-芳基-4H-苯并[h]色烯或苯并[f]色烯衍生物。以苯甲醛、丙二氰与α-萘酚的反应为模板反应,通过单因素实验方案优化了反应的工艺条件。结果表明:反应物各10 mmol,催化剂K2CO3 1 mmol,溶剂无水乙醇15 ml,采用微波功率500 W,80℃回流反应 5 min,2-氨基-3-氰基-4-苯基-4H-苯并[h]色烯(4a)的收率83.6%。在上述最佳条件下,利用取代苯甲醛代替苯甲醛,4H-苯并[h]色烯衍生物(4)产率为65.8%~89.4%。 利用β-萘酚代替α-萘酚,4H-苯并[f]色烯衍生物(6)产率为67.5%~82.9%,合成产物通过熔点和红外光谱表征其结构。

关键词: 微波辐射, 2-氨基-3-氰基-4-芳基-4H-苯并色烯衍生物, 一锅法合成, 碳酸钾催化

Abstract:

A series of 2-amino-4-aryl-3-cyano-4H-benzo[h]chromene or benzo[h]chromene derivatives were synthesized by a three-component one-pot reaction of aromatic aldehydes, malononitrile and α-naphthol(or β-naphthol) with K2CO3 as catalyst in anhydrous ethanol solvent under microwave irradiation. With benzaldehyde, malononitrile and α-naphthol as template reaction, the reaction conditions were optimized by single factor experiments. The results showed that 2-amino-4-aryl-3-cyano-4H-benzo[h]chromene(4a) was obtained 83.6% yield with the condition of each reactant 10 mmol, K2CO3 1 mmol and anhydrous ethanol 15 ml as solvent, using microwave power 500 W, reflux reaction 5 min at 80℃. Under the best of the above conditions,using substituted benzaldehyde to replace benzaldehyde, 4H-benzo[h]chromene derivatives(4) were obtained 65.8%~89.4% yield. Using β-naphthol to replace α-naphthol, 4H-benzo[f]chromene derivatives(6) were obtained 67.5%~82.9% yield. The structures of these compound were characterized by m.p. and IR.

Key words: microwave irradiation, 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives, one-pot synthesis, K2CO3 catalyst

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