4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成

doi:10.6023/cjoc202308010

有机化学 ›› 2024, Vol. 44 ›› Issue (2): 644-649.DOI: 10.6023/cjoc202308010 上一篇下一篇

研究简报

4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成

高宝昌^a^,^b^,^*(), 石雨^b, 田媛^b, 张治国^b, 张婧如^b, 孙宇峰^b, 毛国梁^a, 戴凌燕^c^,^*()

a 东北石油大学化学化工学院黑龙江大庆 163319
b 黑龙江省科学院大庆分院植物化学研究所黑龙江大庆 163319
c 黑龙江八一农垦大学生命科学技术学院黑龙江大庆 163319

收稿日期:2023-08-12 修回日期:2023-10-13 发布日期:2023-11-07
基金资助:
黑龙江省自然科学基金(LH2020B022); 黑龙江省科学院院长基金(YZ2022DQ01); 黑龙江省科学院双提雁阵特别计划基金(YZQY2023DQ01); 黑龙江省省属科研院所科研业务费基金(YS2023DQ02)

Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives

Baochang Gao^a^,^b(), Yu Shi^b, Yuan Tian^b, Zhiguo Zhang^b, Jingru Zhang^b, Yufeng Sun^b, Guoliang Mao^a, Lingyan Dai^c()

a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, Heilongjiang 163319
b Institute of Phytochemistry, Daqing Branch of Heilongjiang Academy of Sciences, Daqing, Heilongjiang 163319
c College of Science and Biotechnology, Heilongjiang Bayi Agricultural University, Daqing, Heilongjiang 163319

Received:2023-08-12 Revised:2023-10-13 Published:2023-11-07
Contact: * E-mail: chemgbc@163.com; dailingyan770416@126.com
Supported by:
Heilongjiang Provincial Natural Science Foundation(LH2020B022); Dean Foundation of Heilongjiang Academy of Sciences(YZ2022DQ01); Shuangtiyanzhen Special Plan Foundation of Heilongjiang Academy of Sciences(YZQY2023DQ01); Institutes Scientific Research Foundation of Heilongjiang Provincial Scientific Research(YS2023DQ02)

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摘要/Abstract

2-吡喃酮衍生物在药物领域表现出了巨大的应用潜力, 已有很多该类骨架结构用作合成药物活性分子前体. 因此, 探索新型2-吡喃酮衍生物的合成方法非常重要. 以β-酮酰胺衍生物和氰基乙酸乙酯为原料一步反应合成了2-吡喃酮衍生物, 具有产物收率高(82%~93%)、反应条件温和产物后处理方便等优点, 为2-吡喃酮生物的合成提供了新策略.

关键词: 2-吡喃酮, β-酮酰胺, 环化

2-Pyrone derivatives have demonstrated considerable potential for usage in the field of medicine. Many of these skeleton structures have been used as precursors in the synthesis of pharmacologically active molecules. As a result, it is critical to explore new approaches for the synthesis of 2-pyrones. A series of 2-pyrone derivatives were synthesized from β-oxo amides and ethyl cyanoacetate through one-step reaction. The methodology offers several significant advantages including mild conditions, ease of handling, and high yields (82%~93%). Such, an efficient synthesis approach for 2-pyrones is provided.

Key words: 2-pyrones, β-oxo amides, cyclization

引用此文

高宝昌, 石雨, 田媛, 张治国, 张婧如, 孙宇峰, 毛国梁, 戴凌燕. 4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成[J]. 有机化学, 2024, 44(2): 644-649.

Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.

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Entry	Base (equiv.)	Solvent	Temp./℃	Yield/%
1	NaOH (1) or KOH (1)	DMF	r.t.	0 or 0
2	NaOH (1) or KOH (1)	DMF	80	Mixture or mixture
3	CsCO₃(1)	C₂H₅OH	50 or reflux	Mixture or 17
4	LiOH (1)	CH₃OH	50 or reflux	Mixture or 20
5	Pyridine (1)	C₂H₅OH	r.t. or 50	0 or mixture
6	Pyridine (1 or 2)	CH₂Cl₂	r.t.	0 or 0
7	DBU (1)	DMF	r.t. or 70	Mixture or mixture
8	DABCO (1)	C₂H₅OH	r.t. or 50	Mixture or mixture
9	DABCO (2)	CH₃OH	reflux	Mixture
10	K₂CO₃ (1)	DMF	r.t. or 50	Mixture or mixture
11	K₂CO₃ (2)	DMF	80 or 110	23 or 31
12	K₂CO₃ (1)	C₂H₅OH	r.t. or reflux	Mixture or 68
13	K₂CO₃ (2)	C₂H₅OH	reflux	67
14	^tBuOK (1)	DMF or C₂H₅OH	80	31 or 44
15	CH₃ONa (1)	CH₃OH	r.t. or 50	25 or 47
16	CH₃ONa (1)	CH₃OH	reflux	52
17	C₂H₅ONa (1)	C₂H₅OH	r.t. or 50	Mixture or 66
18	C₂H₅ONa (1)	C₂H₅OH	reflux	89
19	C₂H₅ONa (0.5 or 2)	C₂H₅OH	reflux	57 or 85
20	C₂H₅ONa (1)	C₂H₅OH	reflux	90^b

Entry	Base (equiv.)	Solvent	Temp./℃	Yield/%
1	NaOH (1) or KOH (1)	DMF	r.t.	0 or 0
2	NaOH (1) or KOH (1)	DMF	80	Mixture or mixture
3	CsCO₃(1)	C₂H₅OH	50 or reflux	Mixture or 17
4	LiOH (1)	CH₃OH	50 or reflux	Mixture or 20
5	Pyridine (1)	C₂H₅OH	r.t. or 50	0 or mixture
6	Pyridine (1 or 2)	CH₂Cl₂	r.t.	0 or 0
7	DBU (1)	DMF	r.t. or 70	Mixture or mixture
8	DABCO (1)	C₂H₅OH	r.t. or 50	Mixture or mixture
9	DABCO (2)	CH₃OH	reflux	Mixture
10	K₂CO₃ (1)	DMF	r.t. or 50	Mixture or mixture
11	K₂CO₃ (2)	DMF	80 or 110	23 or 31
12	K₂CO₃ (1)	C₂H₅OH	r.t. or reflux	Mixture or 68
13	K₂CO₃ (2)	C₂H₅OH	reflux	67
14	^tBuOK (1)	DMF or C₂H₅OH	80	31 or 44
15	CH₃ONa (1)	CH₃OH	r.t. or 50	25 or 47
16	CH₃ONa (1)	CH₃OH	reflux	52
17	C₂H₅ONa (1)	C₂H₅OH	r.t. or 50	Mixture or 66
18	C₂H₅ONa (1)	C₂H₅OH	reflux	89
19	C₂H₅ONa (0.5 or 2)	C₂H₅OH	reflux	57 or 85
20	C₂H₅ONa (1)	C₂H₅OH	reflux	90^b

Entry	1	R	2	Time/h	Yield/%
1	1a	Ph	2a	4	89^a, 90^b
2	1b	4-ClC₆H₄	2b	4.5	91^a, 87^b
3	1c	2-MeC₆H₄	2c	5	93^a, 91^b
4	1d	2-MeOC₆H₄	2d	4	84^a, 82^b
5	1e	2,4-Me₂C₆H₃	2e	4	82^a, 85^b
6	1f	4-MeOC₆H₄	2f	4.5	87^a, 84^b
7	1g	2-ClC₆H₄	2g	5	86^a, 81^b
8	1h	4-MeC₆H₄	2h	4	90^a, 92^b
9	1i	2,5-(MeO)₂-4-ClC₆H₂	2i	5	83^a, 84^b
10	1j	CH₃	2j	5	0

Entry	1	R	2	Time/h	Yield/%
1	1a	Ph	2a	4	89^a, 90^b
2	1b	4-ClC₆H₄	2b	4.5	91^a, 87^b
3	1c	2-MeC₆H₄	2c	5	93^a, 91^b
4	1d	2-MeOC₆H₄	2d	4	84^a, 82^b
5	1e	2,4-Me₂C₆H₃	2e	4	82^a, 85^b
6	1f	4-MeOC₆H₄	2f	4.5	87^a, 84^b
7	1g	2-ClC₆H₄	2g	5	86^a, 81^b
8	1h	4-MeC₆H₄	2h	4	90^a, 92^b
9	1i	2,5-(MeO)₂-4-ClC₆H₂	2i	5	83^a, 84^b
10	1j	CH₃	2j	5	0

4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成

Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives

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