Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt

doi:10.6023/cjoc202111015

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1759-1769.DOI: 10.6023/cjoc202111015 Previous Articles Next Articles

ARTICLES

乙烯基硒盐参与的串联反应合成1-[1-(胺基)环丙基]酮化合物

袁飞, 赵艳, 郭青松, 尹福丹, 赖金荣, 念倍芳, 张明, 汤峨^*()

云南大学教育部自然资源药物化学重点实验室昆明 650091

收稿日期:2021-11-07 修回日期:2022-02-07 发布日期:2022-02-25
通讯作者: 汤峨
作者简介:
† 共同第一作者
基金资助:
长江学者和创新团队发展计划(IRT17R94); 国家自然科学基金(21762046); 国家自然科学基金(22161050); 云南科技厅-云南大学“双一流”建设联合基金(2018FY001); 云南省高校科技创新团队支持计划及云南大学“青年英才”培育计划资助项目

Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt

Fei Yuan, Yan Zhao, Qingsong Guo, Fudan Yin, Jinrong Lai, Beifang Nian, Ming Zhang, E Tang()

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091

Received:2021-11-07 Revised:2022-02-07 Published:2022-02-25
Contact: E Tang
About author:
† These authors contributed equally to this work
Supported by:
Program for Changjiang Scholars and Innovative Research Team in University(IRT17R94); Natural Science Foundation of China(21762046); Natural Science Foundation of China(22161050); Program for Yunnan Provincial Department of Science and Technology-Yunnan University "Double First-Class" Construction Joint Fund(2018FY001); Innovative Research Team(in Science and Technology) in University of Yunnan Province and the Program for the “Young Talent” in Yunnan University

1. .pdf(3063KB)

Abstract

A new one-pot method for the efficient synthesis of 1-(1-(amino)cyclopropyl)ketone compounds has been developed. Under the mediation of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1-(1-(amino)cyclopropyl)ketones were obtained in 70%~93% yields through a reaction sequence of nucleophilic addition/proton migration/nucleophilic substitution and deselenization of β-amino ketones and methyl phenyl vinyl selenium tetrafluoroborate. This method features mild reaction conditions, simple experiment operation, good functional group compatibility. Diphenyl diselenide, the general substrate of the selenium salt reagents, can be prepared by the simple treatment of the by-product methyl phenyl selenide with bromine and hydrazine. Therefore, the vinylselenide salts can be regenerated and reused, which improves the utilization of high-valent selenium reagents and improves the industrial application of this method.

Key words: high valent selenium salt, 1-(1-(amino)cyclopropyl)ketones, one-pot method, tandem reaction

Cite this article

Fei Yuan, Yan Zhao, Qingsong Guo, Fudan Yin, Jinrong Lai, Beifang Nian, Ming Zhang, E Tang. Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1759-1769.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 9

Figure 1. Some medicines and bioactive molecules containing of 1-(1-(amino)cyclopropyl)ketone (or carboxylic acid derivative) scheleton

Scheme 1. Strategies for the synthesis of 1-(1-(amino)cyclo- propyl)ketone compounds

Scheme 2. Reactivity of vinyl selenium cation

Entry	Solvent	Base	T/℃	Time/min	Yield^b/% of 3a
1	DCM	DBU	0	60	89
2	DCM	NaH	0	60	20
3	DCM	TEA	0	60	0
4	DCM	K₂CO₃	0	60	0
5	DCM	Cs₂CO₃	0	60	0
6	THF	DBU	0	60	80
7	CH₃CN	DBU	0	60	62
8	Toluene	DBU	0	60	48
9	DCM	DBU	25	60	87
10	DCM	DBU	0	80	89
11	DCM	DBU	0	40	73
12	DCM	DBU	0	20	40
13^c	DCM	DBU	0	60	42

Table 1. Optimization of the reaction conditions for the synthesis of 1-[1-(amino)cyclopropyl]ketone

Figure 2. Vinyl selenium cations

Table 2. Synthesis of α-amino aryl ketone compounds

Scheme 3. Synthesis of 1-[1-(amino)cyclopropyl]ketone 3a

Scheme 4. Proposed reaction mechanism for the synthesis of 1-[1-(amino)cyclopropyl]ketones

Scheme 5. Synthesis of 2-benzoyl quinolone 5

References 26

[1]	(a) Liu, H.-W.; Walsh, C. T. The Chemistry of the Cyclopropyl Group, Ed.: Rappoport, Z., John Wiley & Sons Ltd., New York, 1987. pmid: 12683792
	(b) Wessjohann, L. A.; Brandt, W. Chem. Rev. 2003, 103, 1625. pmid: 12683792
[2]	Wan, L.-Z.; Wang, H. Chemistry (Huaxue Tongbao) 2019, 82, 963. (in Chinese)
	( 万灵子, 王晗, 化学通报, 2019, 82, 963.)
[3]	(a) Reissig, H. U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
	(b) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603. doi: 10.1021/cr010015v
	(c) Cohen, Y.; Cohen, A.; Marek, I. Chem. Rev. 2021, 121, 140. doi: 10.1021/acs.chemrev.0c00167
	(d) Ebner, C.; Carreira, E. M. Chem. Rev. 2017, 117, 11651. doi: 10.1021/acs.chemrev.6b00798
	(e) Pirenne, V.; Muriel, B.; Waser, J. Chem. Rev. 2021, 121, 227. doi: 10.1021/acs.chemrev.0c00109
[4]	(a) Barone, V.; Fraternali, F.; Cristinziano, P. L.; Lelj, F.; Rosa, A. Biopolymers 1988, 27, 1673. doi: 10.1002/bip.360271011 pmid: 9151253
	(b) Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Crisma, M.; Valle, G.; Toniolo, C. Biopolymers 1989, 28, 175. doi: 10.1002/bip.360280119 pmid: 9151253
	(c) Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287. pmid: 9151253
	(d) Burgess, K.; Ke, C. Y. J. Pept. Res. 1997, 49, 201. pmid: 9151253
[5]	(a) Burgess, K.; Li, W.; Lim, D.; Moye-Sherman, D. Biopolymers 1997, 42, 439. pmid: 11782172
	(b) Martin, S. F.; Dwyer, M. P.; Hartmann, B.; Knight, K. S. J. Org. Chem. 2000, 65, 1305 pmid: 11782172
	(c) Davidson, J. P.; Lubman, O.; Rose, T.; Waksman, G.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 205. pmid: 11782172
[6]	(a) Ner, S. K.; Suckling, C. J.; Bell, A. R.; Wrigglesworth, R. Chem. Commun. 1987, 480.
	(b) Kemp, A.; Tedford, C.; Suckling, C. J. Bioorg. Med. Chem. Lett. 1991, 1, 557. doi: 10.1016/S0960-894X(01)80465-0
	(c) Hilier, M. C.; Davidson, J. P.; Martin, S. F. J. Org. Chem. 2001, 66, 1657. doi: 10.1021/jo001257i
[7]	Andrew, M.; Dominique, G. Nat. Prod. Res. 2005, 19, 639. pmid: 16076632
[8]	Talele, T. T. J. Med. Chem. 2016, 59, 8712. doi: 10.1021/acs.jmedchem.6b00472
[9]	(a) Han, W.; Hu, Z.; Jiang, X.; Wasserman, Z. R.; Decicco, C. P. Bioorg. Med. Chem. Lett. 2003, 13, 1111.
	(b) Lamarre, D.; Anderson, P. C.; Bailey, M.; Beaulieu, P.; Bolger, G.; Bonneau, P.; Bos, M.; Cameron, D. R.; Cariter, M.; Cordingley, M. G.; Faucher, A.-M.; Goudreau, N.; Kawai, S. H.; Kukolj, G.; Lagace, L.; Laplante, S. R.; Narjes, H.; Poupart, M.-A.; Rancourt, J.; Sentjens, R. E.; St George, R.; Simoneau, B.; Steinmann, G.; Thiebeault, D.; Tsantrizos, Y. S.; Weldon, S. M.; Yong, C.-L.; Llinas-Brunet, M. Nature 2003, 426, 186. doi: 10.1038/nature02099
[10]	Kawada, M.; Kawano, Y.; Sugihara, H.; Takei, S.; Imada, I. Chem. Pharm. Bull. 1981, 29, 1900. doi: 10.1248/cpb.29.1900
[11]	Brotherton, C. A.; Wilson, M.; Byrd, G.; Balskus, E. P. Org. Lett. 2015, 17, 1545. doi: 10.1021/acs.orglett.5b00432 pmid: 25753745
[12]	Serusi, L.; Soddu, F.; Cuccu, F.; Peretti, G.; Luridiana, A.; Secci, F.; Caboni, P.; Aitken, D. J.; Frongia, A. Adv. Synth. Catal. 2020, 362, 4159. doi: 10.1002/adsc.202000541
[13]	Mao, Z.-J.; Qu, H.-J.; Zhao, Y.-Y.; Lin, X.-F. Chem. Commun. 2012, 48, 9927. doi: 10.1039/c2cc35235d
[14]	Wirth, T. Organoselenium Chemistry (Synthesis and Reactions), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2012, pp. 204-211.
[15]	(a) Tang, E; Wang, W. L.; Zhao, Y. J.; Zhang, M.; Dai, X. Org. Lett. 2016, 18, 176. doi: 10.1021/acs.orglett.5b03157 pmid: 26882088
	(b) Tang, E; Zhao, Y. J.; Li, W.; Wang, W. L.; Zhang, M.; Dai, X. Org. Lett. 2016, 18, 912. doi: 10.1021/acs.orglett.5b03579 pmid: 26882088
	(c) Tang, E; Zhao, Y. J.; Zhang, M.; Dai, X.; Wang, W. L. Heterocycles 2016, 92, 708. doi: 10.3987/COM-15-13402 pmid: 26882088
	(d) Sun, Q.; Liao, M. H.; Zhao, Y.; Li, Y. X.; Liu, S. S.; Mao, D. S.; Tang, E. Heterocycles 2019, 98, 1563. doi: 10.3987/COM-19-14162 pmid: 26882088
	(e) Liao, M. H.; Zhang, M.; Hu, D. H.; Zhang, R. H.; Zhao, Y.; Liu, S. S.; Li, Y. X.; Xiao, W. L.; Tang, E Org. Biomol. Chem. 2020, 18, 3941. doi: 10.1039/D0OB90071K pmid: 26882088
[16]	(a) Tang, Y.; Ye, S.; Sun, X.-L. Synlett 2005, 2720.
	(b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. doi: 10.1021/cr00094a007
	(c) Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87. doi: 10.1021/cr60287a005
	(d) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611. doi: 10.1021/ar030045f
[17]	Watanabe, S.-I.; Kusumoto, T.; Yoshida, C.; Kataoka, T. Chem. Commun. 2001, 839.
[18]	(a) Borzecka, W.; Lavandera, I.; Gotor, V. J. Org. Chem. 2013, 78, 7312. doi: 10.1021/jo400962c
	(b) Pal, M.; Swamy, N. K.; Hameed, P. S.; Padakanti, S.; Yeleswarapu, K. R. Tetrahedron 2004, 60, 3987. doi: 10.1016/j.tet.2004.03.036
[19]	Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042. doi: 10.1246/bcsj.66.2042
[20]	Gilbert, B. B.; Eey, S. T.-C.; Ryabchuk, P.; Garry, O.; Denmark, S. E. Tetrahedron 2019, 75, 4086.
[21]	(a) Mato, M.; Franchino, A.; Garcı́a-Morales, C.; Echavarren, A. M. Chem. Rev. 2021, 121, 8613.
	(b) Gao, J.-S.; Bian, Q.-H.; Guo, H.-C. Chin. J. Org. Chem. 2007, 27, 438. (in Chinese)
	( 高金山, 边庆花, 郭洪超, 有机化学, 2007, 27, 438.)
	(c) Liang, J.; Ma, H.-F.; Ablajan, K. Chin. J. Org. Chem. 2019, 39, 3169. (in Chinese) doi: 10.6023/cjoc201904028
	( 梁杰, 马会芳, 阿布拉江•克依木, 有机化学, 2019, 39, 3169.) doi: 10.6023/cjoc201904028
	(d) Wang, M.; Chen, J.; Wu, X.-Y.; Deng, H.-M.; Zhang, H.; Shao, M.; Cao, W.-G. Chin. J. Org. Chem. 2009, 29, 1611. (in Chinese)
	( 王猛, 陈杰, 吴小余, 邓红梅, 张慧, 邵敏, 曹卫国, 有机化学, 2009, 29, 1611.)
	(e) Su, G.-F.; Pan, C.-X.; Mou, H.-T.; Zeng, L.-M.; Yu, K.-B. Acta Chim. Sinica 2004, 62, 1941. (in Chinese)
	( 苏桂发, 潘成学, 牟红涛, 曾陇梅, 郁开北, 化学学报, 2004, 62, 1941.)
	(f) Shi, Z.-J.; Liu, M.; Liang, C. Chin. J. Synth. Chem. 2008, 16, 546. (in Chinese)
	( 施志坚, 刘梅, 梁超, 合成化学, 2008, 16, 546.)
	(g) Li, X.-D.; Fan, X.-E.; Zhang, G.-Y.; Chen, Q.-H. Chemistry (Huaxue Tongbao) 2005, 68, 209. (in Chinese)
	( 李晓冬, 范雪娥, 张桂英, 陈庆华, 化学通报, 2005, 68, 209.)
	(h) Gao, T.-Y.; Shi, Z.-J.; Cao, W.-G.; Deng, H.-M. Chin. J. Synth. Chem. 2009, 17, 566. (in Chinese)
	( 高天云, 施志坚, 曹卫国, 姜海燕, 邓红梅, 合成化学, 2009, 17, 566.)
	(i) Zhang, X.-L.; Huang, H.-H.; Chen, Q.-H. Chin. J. Org. Chem. 2002, 22, 411. (in Chinese) doi: 10.1002/cjoc.20040220502
	( 张熊禄, 黄海洪, 陈庆华, 有机化学, 2002, 22, 411.)
	(j) Jin, W.-B.; Yuan, H.; Tang, G.-L. Chin. J. Org. Chem. 2018, 38, 2324. (in Chinese) doi: 10.6023/cjoc201805059
	( 金文兵, 袁华, 唐功利, 有机化学, 2018, 38, 2324.) doi: 10.6023/cjoc201805059
[22]	Luan, B.; Catalina, S.; Lorenzo, T.; Marcello, T. Tetrahedron: Asymmetry 2009, 20, 1506.
[23]	Watanabe, Y.; Ueno, Y.; Toru, T. Bull. Chem. Soc. Jpn. 1993, 66, 2042. doi: 10.1246/bcsj.66.2042
[24]	Francesca, G. N.; Bonifacio, M.; Eder, J. L.; Paul, E.; Claudio, S. Molecules 2020, 25, 2018. doi: 10.3390/molecules25092018
[25]	Guo, S.-Q.; Zhang, N.-N.; Tang, X.-Z.; Mao, Z.-F.; Zhang, X.-J.; Yan, M.; Xuan, Y.-N. Chin. Chem. Lett. 2019, 30, 406. doi: 10.1016/j.cclet.2018.08.021
[26]	Mao, Z.-J.; Qu, H.-J.; Zhao, Y.-Y.; Lin, X.-F. Chem. Commun. 2012, 48, 9927. doi: 10.1039/c2cc35235d

乙烯基硒盐参与的串联反应合成1-[1-(胺基)环丙基]酮化合物

Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 9

References 26

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jinsong Hou, Gaosheng Yang. Reaction of Tandem Addition of Aliphatic Amines to Alkenylnitriles Catalyzed by Tris(o-dimethylaminobenzyl)yttrium [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2070-2078.
[2]	Huijie Qiao, Liting Yang, Ya Chen, Jialin Wang, Wuxuan Sun, Haobo Dong, Yunwei Wang. An Efficient Three-Component Tandem Approach for the Synthesis of Imidazoheterocycle-Hydrazine Derivatives under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1188-1197.
[3]	Xianghao Luo, Yibi Xie, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 838-846.
[4]	Mingliang Wang, Liuyan Yin, Tiantian Wen, Xiao Zhang, Jie Gao, Lanzhi Wang. Green Synthesis of 1,5-Benzodiazepines with Multifunctional Groups [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 160-171.
[5]	Yuyu Guo, Xiangjie Chen, Shiwu Li, Zhihua Cai, Lin He. Synthesis of Mutisubstituted Dihydropyridino[1,2-a]benzimidazole Derivatives via Tandem Reaction of 2-Arylbenzimidazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3692-3700.
[6]	Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.
[7]	Jingru Liang, Bingying Wang, Chengyin Huang, Xiaojun Ye, Yanmei Wen. Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2116-2120.
[8]	Zhiyu Hu, Guofang Jiang, Zhiqiang Zhu, Bozhen Gong, Zongbo Xie, Zhanggao Le. One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 325-332.
[9]	Suyan Zhao, Xueqin Gong, Ziyu Gan, Qiuli Yan, Xueliang Liu, Daoshan Yang. Efficient Copper-Catalyzed Domino Synthesis of Phosphonated Isoquinolin-1(2H)-ones Using Cyanomethylphosphonates as Building Blocks [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 258-266.
[10]	Li Xue, Song Zirui, Chen Xin, Cai Yichao, Liu Yajie, Chen Chunxia, Peng Jinsong. Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 950-958.
[11]	Yang Kai, Yao Chen, Gao Juanjuan, Chen Sihong, Zheng Xuejie, Deng Luxuan, Zhang Yu'na, Liu Meijuan, Wang Zhaoyang. Progress on the Synthesis of Pyrido[1,2-a]benzimidazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4168-4183.
[12]	Zheng Renhua, Guo Haichang, Yang Mingyang, Liu Mengqi, Ye Longwu. 1,4-Functionalization of 3-En-1-ynes with Alcohols via Zinc-Catalyzed Regioselective N-Oxide Oxidation [J]. Chin. J. Org. Chem., 2019, 39(6): 1672-1680.
[13]	Zhu Jianrong, Ren Xiaojuan, Tang Feiyu, Pan Fei, Ye Longwu. Synthesis of α-Halo Amides via Zinc-Mediated Tandem Oxidation/Halogenation of Ynamides [J]. Chin. J. Org. Chem., 2019, 39(4): 1102-1108.
[14]	Su Lin, Hou Wei. Progress in the Synthesis of Cinnoline Derivatives [J]. Chin. J. Org. Chem., 2019, 39(2): 363-376.
[15]	Songbuer, Li Minghui, Imerhasan Mukhtar. Synthesis and Application of Acridine Derivatives [J]. Chin. J. Org. Chem., 2018, 38(3): 594-611.