Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

doi:10.6023/cjoc202404005

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3427-3436.DOI: 10.6023/cjoc202404005 Previous Articles Next Articles

ARTICLE

铜催化苯并呋喃并嘧啶并异吲哚衍生物的合成

何姮, 吕兰兰^*(), 刘建全, 王香善^*()

江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2024-04-05 修回日期:2024-05-14 发布日期:2024-06-13
基金资助:
江苏省优秀青年基金(BK20211607); 江苏省高等学校重点学科建设计划资助项目

Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

Heng He, Lanlan Lü^*(), Jianquan Liu, Xiangshan Wang^*()

School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2024-04-05 Revised:2024-05-14 Published:2024-06-13
Contact: *E-mail:lvll800@126.com;xswang@jsnu.edu.cn
Supported by:
Outstanding Youth Fund of Jiangsu Province(BK20211607); Priority Academic Program Development of Jiangsu Higher Education Institutions.

1. .pdf(4515KB)

Abstract

A copper-catalyzed Sonogashira coupling reaction and 5-exo-dig aminocyclization between 2-(2-bromophenyl)- benzofuro[3,2-d]pyrimidin-4(3H)-ones and terminal alkynes were disclosed. The protocol allowed access to a series of 8-benzylidene benzofuro[3',2':4,5]pyrimido[2,1-a]isoindol-6(8H)-one derivatives with high efficiency, broad substrate scope, and excellent functional group compatibility, which were shown to be of a single (E)-configuration by X-ray diffraction analysis.

Key words: benzofuropyrimidoisoindole, Sonogashira coupling, acetylene hydroamination, CuI

Cite this article

Heng He, Lanlan Lü, Jianquan Liu, Xiangshan Wang. Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3427-3436.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 39

[1]	Jiang X.; Tang T.; Wang J.-M.; Chen Z.; Zhu Y.-M.; Ji S.-J. J. Org. Chem. 2014, 79, 5082. doi: 10.1021/jo500636y pmid: 24810598
[2]	Verma V.; Schafer L. L. J. Org. Chem. 2023, 88, 1378.
[3]	Hosseinzadeh Z.; Ramazani A.; Razzaghi-Asl N. Curr. Org. Chem. 2018, 22, 2256.
[4]	Mermer A.; Keles T.; Sirin Y. Bioorg. Chem. 2021, 114, 105076.
[5]	Parshikov I. A.; Silva E. O.; Furtado N. A. J. C. Appl. Microbiol. Biotechnol. 2014, 98, 1497. doi: 10.1007/s00253-013-5429-1 pmid: 24352731
[6]	Kharazi M.; Saien J.; Asadabadi S. Top. Curr. Chem. 2021, 380, 5.
[7]	Chainikova E.; Safiullin R.; Spirikhin L.; Erastov A. Tetrahedron Lett. 2013, 54, 2140.
[8]	Gordon E. M.; Barrett R. W.; Dower W. J.; Fodor S. P. A.; Gallop M. A. J. Med. Chem. 1994, 37, 1385. pmid: 8182695
[9]	Lai X.; Liu J.-B.; Wang Y.-C.; Qiu G. Chem. Commun. 2021, 57, 2077.
[10]	Ding Q.; Ye Y.; Fan R.; Wu J. J. Org. Chem. 2007, 72, 5439.
[11]	He Y.; Cheng C.; Chen B.; Duan K.; Zhuang Y.; Yuan B.; Zhang M.; Zhou Y.; Zhou Z.; Su Y.-J.; Cao R.; Qiu L. Org. Lett. 2014, 16, 6366.
[12]	Li B.; Zhang J.; Li L.; Chen G. Chem. Sci. 2021, 12, 2504.
[13]	Malet-Martino M.; Jolimaitre P.; Martino R. Curr. Med. Chem.: Anti-Cancer Agents 2002, 2, 267.
[14]	van Kuilenburg A. B. P. Eur. J. Cancer 2004, 40, 939. pmid: 15093568
[15]	Gölcü A.; Muslu H.; Kılıçaslan D.; Çeşme M.; Eren Ö.; Ataş F.; Demirtaş İ. J. Mol. Struct. 2016, 1119, 96.
[16]	Rashid H. u.; Martines M. A. U.; Duarte A. P.; Jorge J.; Rasool S.; Muhammad R.; Ahmad N.; Umar M. N. RSC Adv. 2021, 11, 6060.
[17]	Zhuang J.; Ma S. ChemMedChem 2020, 15, 1875.
[18]	Khanam H.; Shamsuzzaman, Eur. J. Med. Chem. 2015, 97, 483. doi: 10.1016/j.ejmech.2014.11.039 pmid: 25482554
[19]	Xu Z.; Xu D.; Zhou W.; Zhang X. Curr. Top. Med. Chem. 2022, 22, 64.
[20]	Abbas A. A.; Dawood K. M. Expert Opin. Drug Discovery 2022, 17, 1357.
[21]	Cottineau B.; Toto P.; Marot C.; Pipaud A.; Chenault J. Bioorg. Med. Chem. Lett. 2002, 12, 2105. pmid: 12127514
[22]	Xie Y.-S.; Kumar D.; Bodduri V. D. V.; Tarani P. S.; Zhao B.-X.; Miao J.-Y.; Jang K.; Shin D.-S. Tetrahedron Lett. 2014, 55, 2796.
[23]	Koca M.; Servi S.; Kirilmis C.; Ahmedzade M.; Kazaz C.; Özbek B.; Ötük G. Eur. J. Med. Chem. 2005, 40, 1351.
[24]	Xie F.; Zhu H.; Zhang H.; Lang Q.; Tang L.; Huang Q.; Yu L. Eur. J. Med. Chem. 2015, 89, 310.
[25]	Spaniol M.; Bracher R.; Ha H. R.; Follath F.; Krähenbühl S. J. Hepatol. 2001, 35, 628. pmid: 11690709
[26]	Tyltin A. K.; Kovtunenko V. A.; Rytova N. N.; Babichev F. S. Chem. Heterocycl. Compd. 1977, 13, 912.
[27]	Kysil A. I.; Voitenko Z. V.; Wolf J.-G. Collect. Czech. Chem. Commun. 2008, 73, 247.
[28]	Voitenko Z. V.; Kysil A. I.; Wolf J. G. C. R. Chim. 2007, 10, 813.
[29]	He H.; Liu J.-Q.; Wang X.-S. Org. Biomol. Chem. 2023, 21, 7886.
[30]	Geng X.; Shatskiy A.; Alvey G. R.; Liu J.-Q.; Kärkäs M. D.; Wang X.-S. Org. Lett. 2022, 24, 9194. doi: 10.1021/acs.orglett.2c03647 pmid: 36512690
[31]	Chen Y.; Shatskiy A.; Liu J.-Q.; Kärkäs M. D.; Wang X.-S. Org. Lett. 2021, 23, 7555.
[32]	Wang Y.-C.; Chen X.; Alvey G. R.; Shatskiy A.; Liu J.-Q.; Kärkäs M. D.; Wang X.-S. Org. Chem. Front. 2022, 9, 4158.
[33]	Xu L.; Liu X.; Alvey G. R.; Shatskiy A.; Liu J.-Q.; Kärkäs M. D.; Wang X.-S. Org. Lett. 2022, 24, 4513.
[34]	Jiang W.; Li Y.; Liu J.-Q.; Wang X.-S. Org. Lett. 2023, 25, 5123.
[35]	Geng X.; He H.; Shatskiy A.; Stepanova E. V.; Alvey G. R.; Liu J.-Q.; Kärkäs M. D.; Wang X.-S. J. Org. Chem. 2023, 88, 12738.
[36]	Ashfaq U. A.; Javed T.; Rehman S.; Nawaz Z.; Riazuddin S. Virol. J. 2011, 8, 163. doi: 10.1186/1743-422X-8-163 pmid: 21481279
[37]	Cao X.; Zhang Z.; Li J.; Shi B.; Li M.; Zhang G.; Zhang X. J. Org. Chem. 2022, 87, 13672.
[38]	Xiong Y.; Zhang G. Chin. J. Org. Chem. 2023, 43, 1890 (in Chinese).
	(熊阳, 张国柱, 有机化学, 2023, 43, 1890.) doi: 10.6023/cjoc202300028
[39]	Song D.; Moon H.; Jung K.; Yeom M.; Kim H.; Han S.; An D.; Oh J.; Kim J.; Park B.; Kang B. Virol. J. 2011, 8, 1.

Entry	[M]	Ligand	Base	Solvent	Temp./℃	Yield^b/%
1	CuBr	—	K₂CO₃	DMF	50	46
2	CuBr	—	K₂CO₃	DMSO	50	44
3	CuBr	—	K₂CO₃	1,4-Dioxane	50	38
4	CuCl	—	K₂CO₃	DMF	50	35
5	CuI	—	K₂CO₃	DMF	50	50
6	CuBr₂	—	K₂CO₃	DMF	50	27
7	Pd(OAc)₂	—	K₂CO₃	DMF	50	45
8	Pd(PPh₃)₂Cl₂	—	K₂CO₃	DMF	50	39
9	AgOTf	—	K₂CO₃	DMF	50	18
10	CuI	L-Proline	K₂CO₃	DMF	50	53
11	CuI	Pipecolic acid	K₂CO₃	DMF	50	45
12	CuI	o-phen	K₂CO₃	DMF	50	79
13	CuI	2,2'-Bipyridine	K₂CO₃	DMF	50	63
14	CuI	o-phen	Na₂CO₃	DMF	50	73
15	CuI	o-phen	NaHCO₃	DMF	50	68
16	CuI	o-phen	Cs₂CO₃	DMF	50	84
17	CuI	o-phen	Et₃N	DMF	50	60
18	CuI	o-phen	Cs₂CO₃	DMF	60	80
19	CuI	o-phen	Cs₂CO₃	DMF	40	53
20^c	CuI	o-phen	Cs₂CO₃	DMF	50	80

Entry	[M]	Ligand	Base	Solvent	Temp./℃	Yield^b/%
1	CuBr	—	K₂CO₃	DMF	50	46
2	CuBr	—	K₂CO₃	DMSO	50	44
3	CuBr	—	K₂CO₃	1,4-Dioxane	50	38
4	CuCl	—	K₂CO₃	DMF	50	35
5	CuI	—	K₂CO₃	DMF	50	50
6	CuBr₂	—	K₂CO₃	DMF	50	27
7	Pd(OAc)₂	—	K₂CO₃	DMF	50	45
8	Pd(PPh₃)₂Cl₂	—	K₂CO₃	DMF	50	39
9	AgOTf	—	K₂CO₃	DMF	50	18
10	CuI	L-Proline	K₂CO₃	DMF	50	53
11	CuI	Pipecolic acid	K₂CO₃	DMF	50	45
12	CuI	o-phen	K₂CO₃	DMF	50	79
13	CuI	2,2'-Bipyridine	K₂CO₃	DMF	50	63
14	CuI	o-phen	Na₂CO₃	DMF	50	73
15	CuI	o-phen	NaHCO₃	DMF	50	68
16	CuI	o-phen	Cs₂CO₃	DMF	50	84
17	CuI	o-phen	Et₃N	DMF	50	60
18	CuI	o-phen	Cs₂CO₃	DMF	60	80
19	CuI	o-phen	Cs₂CO₃	DMF	40	53
20^c	CuI	o-phen	Cs₂CO₃	DMF	50	80

铜催化苯并呋喃并嘧啶并异吲哚衍生物的合成

Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 39

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Rui Zhang, Mengmeng He, Junjun Xiang, Shali Cai, Congwu Ge, Xike Gao. Core-Expanded Naphthalene Diimides-Vinylogous Tetrathia-fulvalenes toward Ambipolar Organic Semiconductors [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2810-2819.
[2]	Tong Xu, Ning Zhang, Yonghong Zhang, Bin Wang, Yu Xia, Weiwei Jin, Pinru Jin, Chenjiang Liu. Copper-Based Solid Wastes Promoted Cross-Coupling Reactions of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2341-2349.
[3]	Chunming Gui, Tongyao Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jin Huang, Fener Chen. Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2647-2663.
[4]	Hu Zhifang, Peng Lifen, Qiu Renhua, Orita Akihiro. Recent Progress of Protecting Groups for Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3112-3119.
[5]	Xie Zongbo, Li Hongxia, Liu Liansheng, Lan Jin, Hu Zhiyu, Le Zhanggao. Synthesis of Quinazolinone Derivatives Catalyzed by Alkaline Protease [J]. Chin. J. Org. Chem., 2019, 39(9): 2632-2638.
[6]	Liu Ruiting, Li Zhen, Wang Shengke, Zhou Xigeng. Pd(OAc)₂/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3215-3222.
[7]	Kong Shengnan, Malik Abaid Ullah, Qian Xuefeng, Shu Mouhai, Xiao Wende. C-C Coupling Reactions in Water Catalyzed by Palladium [J]. Chin. J. Org. Chem., 2018, 38(2): 432-442.
[8]	Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes [J]. Chin. J. Org. Chem., 2017, 37(7): 1855-1859.
[9]	Zhang Qingyang, Wang Xiaojian, Xiao Qiong, Yin Dali. One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI [J]. Chin. J. Org. Chem., 2017, 37(4): 954-958.
[10]	Yuan Hang, Chen Huilian, Luo Zhibin, Gao Yuhua, Lu Hongfei. Synthesis of a Pd-Pyridine N-Heterocyclic Carbene Complex (NHC)-PdCl₂(Py) and Its Efficient Application in Coupling Reaction [J]. Chin. J. Org. Chem., 2017, 37(11): 2948-2955.
[11]	Xu Xiaolan, Feng Teng, He Jianbo, Xu Huajian. Nano-CuI Catalyzed Cross-Coupling Reaction of Phenols with Nitroarenes [J]. Chin. J. Org. Chem., 2016, 36(5): 1021-1027.
[12]	Guo Ying, Zhu Huaxin, Liu Guilin, Yan Huimin, Zhu Bingjie, Li Shuai, Sun Yajun, Li Guohua. Polymer Solar Cells with High Open-Circuit Voltage Based on Novel Barbell-Shaped Bifullerene Derivative as Acceptor [J]. Chin. J. Org. Chem., 2016, 36(1): 172-178.
[13]	Xu Kai, Shen Chong, Sheng Weijian, Shan Shang, Jia Yixia. Copper-Catalyzed Direct Benzylation of β-Ketoesters with N-Tosylhydrazones [J]. Chin. J. Org. Chem., 2015, 35(3): 633-637.
[14]	Wang Yuanyuan, You Qing, Tao Guide, Zhang Xinming, Zhang Wu. Alkenylation of Heterocycle C—H Catalyzed by CuI Nanoparticles [J]. Chin. J. Org. Chem., 2015, 35(10): 2086-2094.
[15]	Yang Zhenping, Wang Bingnan, Xu Xiaoliang, Wang Hong, Li Xiaonian. Dimerization Coupling Reaction of Terminal Alkyne Promoted by CuI/DEAD [J]. Chin. J. Org. Chem., 2015, 35(1): 207-211.