Base-Promoted Deconstructive Reaction of Exocyclic 1,3-Dicarbonyls for Accessing Hydrazonylated 1,n-Dicarbonyls and Its Biological Evaluation

doi:10.6023/cjoc202404021

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2777-2784.DOI: 10.6023/cjoc202404021 Previous Articles Next Articles

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利用碱促进环外1,3-二羰化合物的解构反应合成腙化的1,n-二羰化合物及其生物活性检测

李平^a^,^*(), 张寅^b, 杨子琪^b, 郝文娟^b, 姜波^b^,^*()

a 河南医学高等专科学校医学系郑州 451191
b 江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2024-04-15 修回日期:2024-05-26 发布日期:2024-06-24
通讯作者: 李平, 姜波
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(21971090); 河南省重点研发与推广专项(科技攻关)(212102310797); 河南省软科学研究计划(242400410409)

Base-Promoted Deconstructive Reaction of Exocyclic 1,3-Dicarbonyls for Accessing Hydrazonylated 1,n-Dicarbonyls and Its Biological Evaluation

Ping Li^a(), Yin Zhang^b, Zi-Qi Yang^b, Wen-Juan Hao^b, Bo Jiang^b()

a Medical Department, Henan Medical College, Zhengzhou 451191
b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2024-04-15 Revised:2024-05-26 Published:2024-06-24
Contact: Ping Li, Bo Jiang
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21971090); Research Project on the Key R & D and Promotion Special Project (Science and Technology Research) of Henan Province(212102310797); Henan Soft Science Research Plan Project(242400410409)

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Abstract

A mild base-promoted three-component deconstructive functionalization of exocyclic 1,3-dicarbonyls with aryl diazonium tetrafluoroborates in the presence of alcohols is reported, enabling direct ring-opening of unstrained cyclic ring systems to produce six types of skeletally diverse hydrazonylated 1,n-diesters (e.g., 1,6-, 1,7- 1,8-, and 1,9-diesters) and 1,n-ketoesters (e.g., 1,6- and 1,7-ketoesters) with good yields, and the latter demonstrated complete (E)-selectivity. The methodology has the potential to be widely used throughout organic synthesis due to the use of easily accessible substrates with different substitution patterns, such as exocyclic 1,3-carbonyls and aryl diazonium tetrafluoroborates, and mild reaction conditions. Preliminary biological evaluation of some compounds, namely their inhibitory effect on human lung cancer cell MSTO-211H, was conducted. The results showed that compounds 3c and 3w exhibited significant inhibitory effects.

Key words: deconstructive reaction, 1,n-diesters, 1,n-ketoesters, stereoselectivity

Cite this article

Ping Li, Yin Zhang, Zi-Qi Yang, Wen-Juan Hao, Bo Jiang. Base-Promoted Deconstructive Reaction of Exocyclic 1,3-Dicarbonyls for Accessing Hydrazonylated 1,n-Dicarbonyls and Its Biological Evaluation[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2777-2784.

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References 17

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Entry	Base (Dosage/equiv.)	Solvent	T/℃	Yield/%
1^b	K₂CO₃ (1.0)	THF/MeOH	r.t.	25
2^b	K₂CO₃ (1.0)	MeCN/MeOH	r.t.	46
3^b	K₂CO₃ (1.0)	DCE/MeOH	r.t.	28
4	K₂CO₃ (1.0)	MeOH	r.t.	72
5	NaOMe (1.0)	MeOH	r.t.	64
6	NaOH (1.0)	MeOH	r.t.	41
7	Na₂CO₃ (1.0)	MeOH	r.t.	60
8	Cs₂CO₃ (1.0)	MeOH	r.t.	81
9	Et₃N (1.0)	MeOH	r.t.	52
10	Cs₂CO₃ (1.5)	MeOH	r.t.	79
11	Cs₂CO₃ (2.0)	MeOH	r.t.	77
12	Cs₂CO₃ (0.5)	MeOH	r.t.	47
13	Cs₂CO₃ (1.0)	MeOH	30	80
14	Cs₂CO₃ (1.0)	MeOH	40	79
15	Cs₂CO₃ (1.0)	MeOH	50	72

Entry	Base (Dosage/equiv.)	Solvent	T/℃	Yield/%
1^b	K₂CO₃ (1.0)	THF/MeOH	r.t.	25
2^b	K₂CO₃ (1.0)	MeCN/MeOH	r.t.	46
3^b	K₂CO₃ (1.0)	DCE/MeOH	r.t.	28
4	K₂CO₃ (1.0)	MeOH	r.t.	72
5	NaOMe (1.0)	MeOH	r.t.	64
6	NaOH (1.0)	MeOH	r.t.	41
7	Na₂CO₃ (1.0)	MeOH	r.t.	60
8	Cs₂CO₃ (1.0)	MeOH	r.t.	81
9	Et₃N (1.0)	MeOH	r.t.	52
10	Cs₂CO₃ (1.5)	MeOH	r.t.	79
11	Cs₂CO₃ (2.0)	MeOH	r.t.	77
12	Cs₂CO₃ (0.5)	MeOH	r.t.	47
13	Cs₂CO₃ (1.0)	MeOH	30	80
14	Cs₂CO₃ (1.0)	MeOH	40	79
15	Cs₂CO₃ (1.0)	MeOH	50	72

Compd.	24 h			48 h
Compd.	1 ng•mL^－1	10 ng•mL^－1	100 ng•mL^－1	1 ng•mL^－1	10 ng•mL^－1	100 ng•mL^－1
Control^a	100	100	100	100	100	100
3b	95.52±4.59	93.56±9.76	88.06±8.79	87.80±6.89	83.81±2.76	74.67±4.07
3c	97.17±6.84	91.44±8.00	86.06±3.48	86.18±6.52	78.89±6.21	67.38±3.79
3e	97.79±5.70	96.62±6.94	94.05±7.30	92.60±1.21	86.24±4.09	81.44±7.68
3g	99.21±4.46	97.54±6.75	92.68±1.49	93.85±7.19	86.22±4.02	80.74±6.29
3i	99.55±3.79	95.88±0.72	94.97±6.83	96.57±1.54	88.53±1.75	86.95±1.67
3k	99.17±5.33	98.22±4.40	95.53±7.81	97.32±4.04	92.08±3.88	84.51±4.59
3n	100.08±8.79	101.63±5.40	99.73±8.85	99.81±5.19	99.42±6.48	98.95±6.92
3o	99.68±1.47	97.10±6.91	94.81±8.10	94.33±3.60	91.26±5.70	83.41±6.01
3w	98.36±6.38	93.50±7.09	86.07±6.87	85.38±5.03	77.27±5.08	70.30±3.12
F value	0.158	0.717	1.546	2.607	6.235	9.182
P value	0.996	0.688	0.199	0.036	0.000	0.000

Compd.	24 h			48 h
Compd.	1 ng•mL^－1	10 ng•mL^－1	100 ng•mL^－1	1 ng•mL^－1	10 ng•mL^－1	100 ng•mL^－1
Control^a	100	100	100	100	100	100
3b	95.52±4.59	93.56±9.76	88.06±8.79	87.80±6.89	83.81±2.76	74.67±4.07
3c	97.17±6.84	91.44±8.00	86.06±3.48	86.18±6.52	78.89±6.21	67.38±3.79
3e	97.79±5.70	96.62±6.94	94.05±7.30	92.60±1.21	86.24±4.09	81.44±7.68
3g	99.21±4.46	97.54±6.75	92.68±1.49	93.85±7.19	86.22±4.02	80.74±6.29
3i	99.55±3.79	95.88±0.72	94.97±6.83	96.57±1.54	88.53±1.75	86.95±1.67
3k	99.17±5.33	98.22±4.40	95.53±7.81	97.32±4.04	92.08±3.88	84.51±4.59
3n	100.08±8.79	101.63±5.40	99.73±8.85	99.81±5.19	99.42±6.48	98.95±6.92
3o	99.68±1.47	97.10±6.91	94.81±8.10	94.33±3.60	91.26±5.70	83.41±6.01
3w	98.36±6.38	93.50±7.09	86.07±6.87	85.38±5.03	77.27±5.08	70.30±3.12
F value	0.158	0.717	1.546	2.607	6.235	9.182
P value	0.996	0.688	0.199	0.036	0.000	0.000

利用碱促进环外1,3-二羰化合物的解构反应合成腙化的1,n-二羰化合物及其生物活性检测

Base-Promoted Deconstructive Reaction of Exocyclic 1,3-Dicarbonyls for Accessing Hydrazonylated 1,n-Dicarbonyls and Its Biological Evaluation

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