Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds

doi:10.6023/cjoc201708046

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 190-199.DOI: 10.6023/cjoc201708046 Previous Articles Next Articles

Special Issue: 庆祝吴养洁院士九十华诞专辑

Articles

金催化的扩环反应:2,3-苯并二氮杂(艹卓)类化合物的高效合成

胡辉, 胡晓苹, 陈铭, 孙宁, 刘元红

中国科学院上海有机化学研究所金属有机化学国家重点实验室中国科学院大学上海 200032

收稿日期:2017-08-23 修回日期:2017-09-25 发布日期:2017-10-11
通讯作者: 孙宁, 刘元红 E-mail:sunning@sioc.ac.cn;yhliu@sioc.ac.cn
基金资助:
国家自然科学基金（Nos.21572256，21372244，21421091）、国家重点研发计划（No.2016YFA0202900）及中国科学院战略性先导科技专项（B类）（No.XDB20000000）资助项目.

Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds

Hu Hui, Hu Xiaoping, Chen Ming, Sun Ning, Liu Yuanhong

State Key Laboratory of Organometallic Chemistry, Shanghai Inistitute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Shanghai 200032

Received:2017-08-23 Revised:2017-09-25 Published:2017-10-11
Contact: 10.6023/cjoc201708046 E-mail:sunning@sioc.ac.cn;yhliu@sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572256, 21372244, 21421091), the National Key R&D Program of China (No. 2016YFA0202900) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000).

1. Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds.PDF(1528KB)

Abstract

A gold-catalyzed oxidative ring expansion of 1-alkynyl-1,2-dihydrophthalazines has been developed. The reaction was catalyzed by PPh₃AuNTf₂in the presence of 8-methylquinoline N-oxide as the oxidant, leading to 2,3-benzodiazepine derivatives with high efficiency. The reaction likely proceeds through the formation of α-carbonyl gold carbene and 1,2-migration of a phenyl group, while no 1,2-H and 1,2-N migration take place. Further transformation of 2,3-benzodiazepine products in the presence of FeCl₃ was also carried out, pyrazole and polyfused heterocycle were formed, respectively, through variation of the amounts of FeCl₃.

Key words: gold catalysis, oxidation, ring expansion, 2,3-benzodiazepine

Cite this article

Hu Hui, Hu Xiaoping, Chen Ming, Sun Ning, Liu Yuanhong. Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds[J]. Chin. J. Org. Chem., 2018, 38(1): 190-199.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Pellow, S.; File, S. E. Pharmacol., Biochem. Behav. 1986, 24, 525.
(b) Chimirri, A.; De Sarro, G.; De Sarro, A.; Gitto, R.; Grasso, S.; Quartarone, S.; Zappalá, M.; Giusti, P.; Libri, V.; Constanti, A.; Chapman, A. G. J. Med. Chem. 1997, 40, 1258.
(c) Zappalá, M.; Grasso, S.; Micale, N.; Polimeni, S.; De Micheli, C. Mini-Rev. Med. Chem. 2001, 1, 243.
[2] Sólyyom, S.; Tarnawa, I. Curr. Pharm. Design 2002, 913.
[3] Howes, J. F.; Bell, C. Neurotherapeutics 2007, 4, 126.
[4] Csuzdi, E.; Migléczi, K.; Hazai, I.; Berzsenyi, P.; Pallagi, I. Bioorg. Med. Chem. Lett. 2005, 15, 4662.
[5] (a) Archer, G. A.; Sternbach, L. H. Chem. Rev. 1968, 68, 747.
(b) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997.
[6] (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A. Org. Lett. 2016, 18, 3511.
(b) Guo, P.; Zeng, X.; Chen, S.; Luo, M. J. Organomet. Chem. 2014, 751, 438.
[7] (a) Snieckus, V.; Streith, J. Acc. Chem. Res. 1981, 14, 348.
(b) Sugimoto, K.; Hayashi, R.; Nemoto, H.; Toyooka, N.; Matsuya, Y. Org. Lett. 2012, 14, 3510.
(c) Guo, C.; Sahoo, B.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17402.
(d) Li, Z.; Yu, H.; Feng, Y.; Hou, Z.; Zhang, L.; Yang, W.; Wu, Y.; Xiao, Y.; Guo, H. RSC Adv. 2015, 5, 34481.
[8] (a) Horváth, E. J.; Horváth, K.; Hámori, T.; Fekete, M. I. K.; Sólyom, S.; Palkovits, M. Prog. Neurobiol. 2000, 60, 309.
(b) Okuma, K.; Tanabe, Y.; Nagahora, N.; Shioji, K. Bull. Chem. Soc. Jpn. 2015, 88, 1064.
(c) Chan, C.-K.; Tsai, Y.-L.; Chan, Y.-L.; Chang, M.-Y. J. Org. Chem. 2016, 81, 9836.
(d) Wang, J.; Wang, L.; Guo, S.; Zha, S.; Zhu, J. Org. Lett. 2017, 19, 3640.
[9] For recent reviews on gold-catalyzed reactions, see:(a) Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115, 9028.
(b) Wang, Y.; Muratore, M. E. Echavarren, A. M. Chem.-Eur. J. 2015, 21, 7332.
(c) Pflästerer, D.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 1331.
(d) Wu, W-T.; Zhang, L.; You, S-L. Acta Chim. Sinica 2017, 75, 419(in Chinese).(吴文挺, 张立明, 游书力, 化学学报, 2017, 75, 419.)
[10] For recent papers, see:gold-catalyzed ring expansion reactions without oxidant:(a) Markham, J. P.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 9708.
(b) Kleinbeck, F.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 9178.
(c) Barluenga, J.; Tudela, E.; Vicente, R.; Ballesteros, A.; Tomás, M. Angew. Chem., Int. Ed. 2011, 50, 2107.
Diphenylsulfoxide as the oxidant:(d) Witham, C. A.; Mauleοn, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
(e) Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156.
Quinoline/pyridine N-oxide as the oxidant:(f) Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258.
(g) Vasu, D.; Hung, H.-H.; Bhunia, S.; Gawade, S. A.; Das, A.; Liu, R.-S. Angew. Chem., Int. Ed. 2011, 50, 6911.
(h) Qian, D.; Zhang, J. Chem. Commun. 2011, 47, 11152.
(i) Yuan, W.; Dong, X.; Wei, Y.; Shi, M. Chem.-Eur. J. 2012, 18, 10501.
Nitrone as the oxidant:(j) Yeom, H.-S.; Lee, J.-E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040.
(k) Chen, D.; Song, G.; Jia, A.; Li, X. J. Org. Chem. 2011, 76, 8488.
[11] Chen. M.; Chen, Y.; Sun, N.; Zhao, J.; Liu, Y; Li, Y. Angew. Chem., Int. Ed. 2015, 54, 1200.
[12] Chen, M.; Sun, N.; Xu, W.; Zhao, J.; Wang, G.; Liu, Y. Chem.-Eur. J. 2015, 21, 18571.
[13] Zhao, J.; Liu, J.; Xie, X.; Li, S.; Liu, Y. Org. Lett. 2015, 17, 5926.
[14] Braunstein, P.; Lehner, H.; Matt, D.; Burgess, K.; Ohlmeyer, M. J. Inorg. Synth. 1990, 27, 218.
[15] Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
[16] Henrion, G.; E. J. Chavas, T.; Goff, X. L.; Gagosz, F. Angew. Chem., Int. Ed. 2013, 52, 6277.

金催化的扩环反应:2,3-苯并二氮杂(艹卓)类化合物的高效合成

Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[2]	Xiaoyu Zhang, Xinyan Li, Bing Cui, Zhihui Shao, Mingqin Zhao. Design, Synthesis and Antioxidant Activity of Tetrahydro-β-carbolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2885-2894.
[3]	Yanhua Gao, Yinpan Zhang, Yan Zhang, Tao Song, Yong Yang. Visible-Light-Induced Aerobic Oxidation of Alcohols over Surface Oxygen Vacancies-Enriched Nb₂O₅ [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2572-2579.
[4]	Ke Jing, Panke Zhang, Senmiao Xu. Application of 1,4-Azaborines in Organic and Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1742-1750.
[5]	Zhihua Chen, Yan Hu, Lili Ma, Ziyi Zhang, Chuanxiang Liu. Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 718-724.
[6]	Bin Wei, Zilong Zhou, Jinghao Qin, Zeyu Yan, Jiacheng Guo, Shu Lei, Yexiang Xie, Xuanhui Ouyang, Renjie Song. Electrochemical Oxidative C(sp³)—H Sulfonylation of Xanthenes with Sodium Sulfinates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 186-194.
[7]	Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.
[8]	Xiaoting Qin, Ning Zou, Caimei Nong, Dongliang Mo. Recent Advances on the Synthesis of Nine-Membered N-Heterocycles [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 130-155.
[9]	Tingshu Cao, Xiangyang Wei, Min Luo, Yifei Wang, Zijun Pan, Cheng Xu, Guodong Yin. PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2079-2088.
[10]	Wucheng Xie, Xu Chen, Yunyue Li, Jieling Lin, Wanwen Chen, Junjun Shi. Electrooxidative Annulation of Unsaturated Molecules via Directed C—H Activation [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1286-1306.
[11]	Yi Zhou, Zhuojun Li, Minghui Hu, Zhaohua Yan, Sen Lin. Oxidation of Sulfides with SO₂F₂/H₂O₂/Base [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1545-1550.
[12]	Ruiqin Zhang, Renchao Ma, Qinjiao Fu, Jing Chen, Yongmin Ma. I₂/PhNO₂ Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 854-862.
[13]	Honghua Zuo, Fangrui Zhong. Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 665-678.
[14]	Xinlei Liu, Leichuan Xu, Xinkun An, Jiazhen Jiang, Ming'an Wang. Synthesis and Larvicidal Activity of Palmarumycin B₆ Analogues [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 519-525.
[15]	Chengjun Zhao, Zhiqin Bai, Jian He, Qiang Liu. Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4300-4314.