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

doi:10.11949/j.issn.0438-1157.20181418

摘要/Abstract

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

中图分类号:

O 625.6

曾育才, 刘小玲, 梁奇峰, 吕鉴泉. 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[J]. 化工学报, 2019, 70(S1): 110-114.

Yucai ZENG, Xiaoling LIU, Qifeng LIANG, Jianquan LYU. One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K₂CO₃ under microwave irradiation[J]. CIESC Journal, 2019, 70(S1): 110-114.

图/表 7

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序号	时间/min	产率/%
1	3	65.5
2	5	83.6
3	8	79.4
4	10	76.0
5	12	71.5

序号	时间/min	产率/%
1	3	65.5
2	5	83.6
3	8	79.4
4	10	76.0
5	12	71.5

序号	功率/W	产率/%
1	200	46.8
2	300	65.6
3	400	77.4
4	500	83.6
5	600	78.5

序号	功率/W	产率/%
1	200	46.8
2	300	65.6
3	400	77.4
4	500	83.6
5	600	78.5

序号	温度/℃	产率/%
1	70	56.8
2	75	63.2
3	80	83.6
4	85	82.5
5	90	72.5