One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction

doi:10.6023/cjoc202006040

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 806-818.DOI: 10.6023/cjoc202006040 Previous Articles Next Articles

Article

三组分串联反应一锅合成多环稠合的1,5-苯并二氮杂䓬化合物

李静¹, 郝振芳¹, 张凯悦¹, 王兰芝¹^,^*()

1 河北师范大学化学与材料科学学院河北省有机功能分子重点实验室石家庄 050024

收稿日期:2020-06-20 修回日期:2020-09-03 发布日期:2020-10-15
通讯作者: 王兰芝
作者简介:
* Corresponding author. E-mail: wanglanzhi@126.com
基金资助:
国家自然科学基金(21776060); 河北省自然科学基金(B2016205165)

One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction

Jing Li¹, Zhenfang Hao¹, Kaiyue Zhang¹, Lanzhi Wang¹^,^*()

1 Laboratory of Organic Functional Molecules of Hebei Province, College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang, Hebei 050024

Received:2020-06-20 Revised:2020-09-03 Published:2020-10-15
Contact: Lanzhi Wang
Supported by:
the National Natural Science Foundation of China(21776060); the Natural Science Foundation of Hebei Province(B2016205165)

1. cjoc202006040.pdf(5848KB)

Abstract

43 novel 1,5-benzodiazepine compounds were obtained via one-pot multicomponent and tadem reactions for 2~5 h and the yield of the target compounds is up to 95%. These reactions were achieved by reacting substituted 1,2-phenylene- diamines, 1,3-cyclopentanedione or 1,3-cyclohexanedione (5,5-dimethyl-1,3-cyclohexanedione), 2,3-dicarbonyl compounds with p-toluenesulfonic acid as catalyst in EtOH. The active intermediates with the imine and enamine structures in the molecule were formed by two nucleophilic addition-dehydration processes and then 1,5-benzodiazepine compounds were obtained via carbon-carbon coupling cyclization and proton transfer processes, which realized the construction of one new seven- membered ring and four new chemical bonds (two C—N, one C=C, one C—C) in one-pot. It provides a green, environmentally friendly, efficient and simple synthetic thought for the synthesis of 1,5-benzodiazepine compounds.

Key words: 1,5-benzodiazepine compound, tadem reaction, green synthesis, mechanism

Cite this article

Jing Li, Zhenfang Hao, Kaiyue Zhang, Lanzhi Wang. One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 806-818.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 21

[1]	Wang K.X.; Wang L.Z. Chin. J. Org. Chem. 2019, 39, 1147. (in Chinese) doi: 10.6023/cjoc201809038 pmid: 5C3905C4-3AAA-4459-A30B-B8D2D6DC7D08
	王凯旋, 王兰芝, 有机化学, 2019, 39, 1147.). doi: 10.6023/cjoc201809038 pmid: 5C3905C4-3AAA-4459-A30B-B8D2D6DC7D08
[2]	Reen G.K.; Ahuja M.; Kumar A.; Patidar R.; Sharma P. Org. Prep. Proced. Int. 2017, 49, 273. doi: 10.1080/00304948.2017.1320927
[3]	Praveen C.; Nandakumar A.; Dheenkumar P.; Muralidharan D.; Perumal P.T. J. Chem. Sci. 2012, 124, 609. doi: 10.1007/s12039-012-0251-3
[4]	Wang N.; Arulkumar M.; Chen X.Y.; Wang B.W.; Chen S.H.; Yao C.; Wang Z.Y. Chin. J. Org. Chem. 2019, 39, 2771. (in Chinese) doi: 10.6023/cjoc201904061 pmid: BC8398ED-3A73-4294-9632-8B4D858A4B4D
	王能, Arulkumar, M., 陈孝云, 王柏文, 陈思鸿, 姚辰, 汪朝阳, 有机化学, 2019, 39, 2771.). doi: 10.6023/cjoc201904061 pmid: BC8398ED-3A73-4294-9632-8B4D858A4B4D
[5]	Tseng C.H.; Lin C.K.; Chen Y.L.; Hsu C.Y.; Wu H.N.; Tseng C.K.; Lee J.C. Eur. J. Med. Chem. 2014, 79, 66. doi: 10.1016/j.ejmech.2014.03.074
[6]	Giroux S.; Xu J.; Reddy T.J.; Morris M.; Cottrell K.M.; Cadilhac C.; Henderson J.A.; Nicolas O.; Bilimoria D.; Denis F.; Mani N.; Ewing N.; Shawgo R.; L'Heureux L.; Selliah S.; Chan L.; Chauret N.; Berlioz-Seux F.; Namchuk M.N.; Grillot A.-L.; Bennani Y.L.; Das S.K.; Maxwell J.P. ACS Med. Chem. Lett. 2014, 5, 240. doi: 10.1021/ml300461f pmid: 24900811
[7]	Yin L.Y.; Wang L.Z. Tetrahedron Lett. 2016, 57, 5935. doi: 10.1016/j.tetlet.2016.11.089
[8]	Fontaine R.; Mercier P.; Beaudry P.; Annable L.; Chouinard G. Acta Psychiatr. Scand. 1986, 74, 2.
[9]	Nguema Ongone, T.; Achour, R.; El Ghoul, M.; El Ouasif, L.; Taghzouti, K.; El Jemli, M.; Cherrah, Y.; Alaoui, K.; Zellou, A. Adv. Pharmacol. Sci. 2018, 2018, 6042602.
[10]	Indalkar K.S.; Patil M.S.; Chaturbhuj G.U. Tetrahedron Lett. 2017, 58, 4496. doi: 10.1016/j.tetlet.2017.10.030
[11]	Shearer C.; Desaunay O.; Zorc S.; Richaud A.D.; Samanta S.S.; Jeedimalla N.; Roche S.P. Tetrahedron 2019, 75, 43.
[12]	Zhou L.Y.; Wang M.L.; Wang K.X.; Wen T.T.; Wang L.Z. Appl. Organomet. Chem. 2020, 34, e5757.
[13]	Wu H.T.; Wang L.Z. New J. Chem. 2020, 44, 10428. doi: 10.1039/C9NJ06332C
[14]	Yin L.Y. M.S. Thesis, Hebei Normal University, Shijiazhuang, 2017. (in Chinese)
	尹刘燕, 硕士论文, 河北师范大学, 石家庄, 2017.).
[15]	He L. M.S. Thesis, Hebei Normal University, Shijiazhuang, 2019. (in Chinese)
	何林, 硕士论文, 河北师范大学, 石家庄, 2019.).
[16]	Sun Y.W.; Zhou L.Y.; Wang L.Z. Chin. J. Org. Chem. 2019, 39, 3516. (in Chinese) doi: 10.6023/cjoc201904026 pmid: 58004467-964E-4682-B3F1-C24DA6F65D6A
	孙悦玮, 周来运, 王兰芝, 有机化学, 2019, 39, 3516.). doi: 10.6023/cjoc201904026 pmid: 58004467-964E-4682-B3F1-C24DA6F65D6A
[17]	Sun Y.W.; Wang L.Z. New J. Chem. 2018, 42, 20032. doi: 10.1039/C8NJ04893B
[18]	Leyva-Perez A.; Cabrero-Antonino J.R.; Corma A. Tetrahedron 2010, 66, 8203. doi: 10.1016/j.tet.2010.08.022
[19]	Fader L.D.; Bethell R.; Bonneau P.; Bos M.; Bousquet Y.; Cordingley M.G.; Coulombe R.; Deroy P.; Faucher A.M.; Gagnon A.; Goudreau N.; Grand-Maitre C.; Guse I.; Hucke O.; Kawai S.H.; Lacoste J.E.; Landry S.; Lemke C.T.; Malenfant E.; Mason S.; Morin S.; O'Meara J.; Simoneau B.; Titolo S.; Yoakim C. Bioorg. Med. Chem. Lett. 2011, 21, 398. doi: 10.1016/j.bmcl.2010.10.131
[20]	Schimer J.; Cigler P.; Vesely J.; Saskova K.G.; Lepsik M.; Brynda J.; Rezacova P.; Kozisek M.; Cisarova I.; Oberwinkler H.; Kraeusslich H.G.; Konvalinka J. J. Med. Chem. 2012, 55, 10130. doi: 10.1021/jm301249q
[21]	McGowan D.; Nyanguile O.; Cummings M.D.; Vendeville S.; Vandyck K.; Van den Broeck W.; Boutton C.W.; De Bondt H.; Quirynen L.; Amssoms K.; Bonfanti J.-F.; Last S.; Rombauts K.; Tahri A.; Hu L.; Delouvroy F.; Vermeiren K.; Vandercruyssen G.; Van der Helm L.; Cleiren E.; Mostmans W.; Lory P.; Pille G.; Van Emelen K.; Fanning G.; Pauwels F.; Lin T.I.; Simmen K.; Raboisson P. Bioorg. Med. Chem. Lett. 2009, 19, 2492. doi: 10.1016/j.bmcl.2009.03.035

Entry	Solvent	Temp./℃	Catalyst^b	Time/h	Yield^c/%
1	EtOH	r.t.	Free	9	30
2	EtOH	r.t.	Et₃N^d	—	—
3	EtOH	r.t.	CeCl₃	6	65
4	EtOH	r.t.	PMA	5	60
5	EtOH	r.t.	Mandelic acid	4	75
6	EtOH	r.t.	PTSA	3	90
7	EtOH	–10	PTSA	24	53
8	EtOH	0	PTSA	17	57
9	EtOH	Reflux	PTSA	2	64
10	MeOH	r.t.	PTSA	3	90
11	PhMe	r.t.	PTSA	4.5	73
12	MeCN	r.t.	PTSA	4	70

Entry	Solvent	Temp./℃	Catalyst^b	Time/h	Yield^c/%
1	EtOH	r.t.	Free	9	30
2	EtOH	r.t.	Et₃N^d	—	—
3	EtOH	r.t.	CeCl₃	6	65
4	EtOH	r.t.	PMA	5	60
5	EtOH	r.t.	Mandelic acid	4	75
6	EtOH	r.t.	PTSA	3	90
7	EtOH	–10	PTSA	24	53
8	EtOH	0	PTSA	17	57
9	EtOH	Reflux	PTSA	2	64
10	MeOH	r.t.	PTSA	3	90
11	PhMe	r.t.	PTSA	4.5	73
12	MeCN	r.t.	PTSA	4	70


5aaa, 2 h, 90%	5baa, 2 h, 92%	5caa, 1.5 h, 90%	5daa, 2 h, 86%	5eaa, 3 h, 74%

5faa,3 h, 80%	5gaa, 4 h, 70%	5haa, 4 h, 80%	5aab, 3 h, 90%	5bab, 3 h, 90%

5cab, 2 h, 90%	5dab, 4 h, 88%	5eab, 3 h, 80%	5fab, 3.5 h, 77%	5gab, 4 h, 72%

5aba, 2 h, 90%	5bba, 1.5 h, 92%	5cba, 1.5 h, 95%	5dba, 3 h, 88%	5eba, 2 h, 83%

5fba, 2 h, 86%	5gba, 4 h, 77%	5abb, 1.5 h, 88%	5bbb, 2.5 h, 90%	5cbb, 3 h, 90%

5dbb, 3 h, 82%	5ebb, 2.5 h, 78%	5fbb, 3 h, 80%	5gbb, 5 h, 75%	5aca, 3 h, 90%


5aaa, 2 h, 90%	5baa, 2 h, 92%	5caa, 1.5 h, 90%	5daa, 2 h, 86%	5eaa, 3 h, 74%

5faa,3 h, 80%	5gaa, 4 h, 70%	5haa, 4 h, 80%	5aab, 3 h, 90%	5bab, 3 h, 90%

5cab, 2 h, 90%	5dab, 4 h, 88%	5eab, 3 h, 80%	5fab, 3.5 h, 77%	5gab, 4 h, 72%

5aba, 2 h, 90%	5bba, 1.5 h, 92%	5cba, 1.5 h, 95%	5dba, 3 h, 88%	5eba, 2 h, 83%

5fba, 2 h, 86%	5gba, 4 h, 77%	5abb, 1.5 h, 88%	5bbb, 2.5 h, 90%	5cbb, 3 h, 90%

5dbb, 3 h, 82%	5ebb, 2.5 h, 78%	5fbb, 3 h, 80%	5gbb, 5 h, 75%	5aca, 3 h, 90%


5bca, 2 h, 92%	5cca, 2 h, 90%	5dca, 3 h, 88%	5eca, 3.5 h, 81%	5fca, 3 h, 86%

5gca, 4.5 h, 80%	5acb, 3 h, 88%	5bcb, 3 h, 88%	5ccb, 2 h, 90%	5dcb, 3.5 h, 83%

5ecb, 3.5 h, 83%	5fcb, 3 h, 83%	5gcb, 5 h, 80%

三组分串联反应一锅合成多环稠合的1,5-苯并二氮杂䓬化合物

One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 21

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[2]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[3]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[4]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[5]	Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1341-1364.
[6]	Jian Ji, Jinhua Liu, Cong Guan, Xuwen Chen, Yun Zhao, Shunying Liu. High Regioselective Synthesis of N²-Substituted-1,2,3-triazole via N-Sulfonyl-1,2,3-triazole Coupling with Alcohol Catalyzed by in-situ Generated Sulfonic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1168-1176.
[7]	Guanghui Shi, Yunzhe Du, Yuanyuan Gao, Huijie Jia, Hailong Hong, Limin Han, Ning Zhu. Reduction of Nitro Group by Sulfide and Its Applications in Amine Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 491-502.
[8]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.
[9]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[10]	Shuo Li, Mingliang Wang, Laiyun Zhou, Lanzhi Wang. Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3977-3988.
[11]	Zehui Li, Haoyu Zou, Lincai Li, Yiling Zhao, Hongping Zhu. Synthesis and Propylene Oxide Carbonylation Hydroesterification Catalytic Property of N,O-Ligand Coordination Cobalt Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3907-3915.
[12]	Saimi Naibijiang, Lei Zhang, Shalamu Maidina, Jing Zeng, Abudu Rexit Abulikemu. Green Synthesis of Thiosulfonates and Sulfonyl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 236-243.
[13]	Lin Ling, Jian Wang, Jing Li, Yuxue Li, Long Lu. Broken-Symmetry Density Functional Theory Study on Pyrolysis Mechanisms of 3-Nitro-1,2,4-triazol-5-one (NTO) [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 285-294.
[14]	Jiantao Zhang, Cong Zhang, Zidong Zheng, Peng Zhou, Weibing Liu. Research Progress of Sulfoxonium Ylides in the Construction of Five/Six-Membered Nitrogen-Containing Heterocycles [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2745-2759.
[15]	Zhentao Pan, Tong Liu, Yongmin Ma, Jianbo Yan, Ya-Jun Wang. Construction of Quinazolin(thi)ones by Brønsted Acid/Visible-Light Photoredox Relay Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2823-2831.