One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions

doi:10.6023/cjoc201608020

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1565-1570.DOI: 10.6023/cjoc201608020 Previous Articles Next Articles

Notes

无催化条件下三组分一锅法合成呋喃并吡啶并喹喔啉衍生物

张梅梅^a, 王洁^b, 刘建全^a, 王香善^a

a. 江苏师范大学化学化工学院徐州 221116;
b. 江苏师范大学科文学院徐州 221116

收稿日期:2016-08-24 修回日期:2016-12-24 发布日期:2017-02-08
通讯作者: 王香善 E-mail:xswang@jsnu.edu.cn
基金资助:
江苏省高校重大基础自然科学基金（No.14KJA150004）、江苏师范大学校自然科学基金（No.15XLA05）资助项目.

One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions

Zhang Meimei^a, Wang Jie^b, Liu Jianquan^a, Wang Xiangshan^a

a. School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116;
b. Kewen College, Jiangsu Normal University, Xuzhou 221116

Received:2016-08-24 Revised:2016-12-24 Published:2017-02-08
Contact: 10.6023/cjoc201608020 E-mail:xswang@jsnu.edu.cn
Supported by:
Project supported by the Major Basic Natural Science Foundation of University in Jiangsu Province (No. 14KJA150004) and the Natural Science Foundation of Jiangsu Normal University (No. 15XLA05).

1. One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions.PDF(680KB)

Abstract

A series of 11-aryl-8,11-dihydrofuro[3',4':5,6]pyrido[3,2-f]quinoxalin-10(7H)-one derivatives were obtained via a one-pot and three-component reaction of aromatic aldehydes, 6-aminoquinoxaline and tetronic acid in EtOH. The structure of 11-(4-nitrophenyl)-8,11-dihydrofuro[3',4':5,6]pyrido[3,2-f]quinoxalin-10(7H)-one (4g) was confirmed by X-ray diffraction analysis. This procedure had the advantages of operation simplicity, catalyst-free and without isolating intermediates, and provided a good method for the synthesis of fused tetracyclic heterocycles containing furan, pyridine and quinoxaline moieties at the same time.

Key words: furopyridoquinoxaline, 6-aminoquinoxaline, three-component reaction, crystal structure, synthesis

Cite this article

Zhang Meimei, Wang Jie, Liu Jianquan, Wang Xiangshan. One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions[J]. Chin. J. Org. Chem., 2017, 37(6): 1565-1570.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Hantzsch, A. Ann. 1882, 215, 72.
[2] (a) Quinonero, O.; Jean, M.; Vanthuyne, N.; Roussel, C.; Bonne, D.; Constantieux, T.; Bressy, C.; Bugaut, X.; Rodriguez, J. Angew. Chem., Int. Ed. 2016, 55, 1401.
(b) Heravi, M. M.; Hosseini, M.; Oskooie, H. A.; Baghernejad, B.; Farzaneh, F. Chin. J. Chem. 2010, 28, 2045.
(c) Wu, J.; Wang, W. Z.; Sun, W. Chin. J. Chem. 2007, 25, 1072.
(d) Guo, S. R.; Yuan, Y. Q.; Zhang, C. N.; Wu, X. M.; Sun, C. Chin. J. Chem. 2010, 28, 811.
(e) Yoo, J. S.; Laughlin, T. J.; Krob, J. J.; Mohan, R. S. Tetrahedron Lett. 2015, 56, 4060.
(f) Yadav, D. K.; Patel, R.; Srivastava, V. P.; Watal, G.; Yadav, L. D. S. Chin. J. Chem. 2011, 29, 118.
[3] (a) Wang, X. S.; Zhang, M. M.; Zeng, Z. S.; Shi, D. Q.; Tu, S. J.; Wei, X. Y.; Zong, Z. M. Tetrahedron Lett. 2005, 46, 7169.
(b) Peng, J. H.; Hao, W. J.; Wang, X. S.; Tu, S. J.; Ma, N.; Zhang, G. Chin. J. Chem. 2009, 27, 1707.
(c) Zhou, Y. J.; Chen, D. S.; Li, Y. L.; Liu, Y.; Wang, X. S. ACS Comb. Sci. 2013, 15, 498.
(d) Shi, F.; Yan, S.; Zhou, D. X.; Tu, S. J.; Zou, X.; Hao, W. J.; Zhang, X. H.; Han, Z. G.; Wu, S. S.; Cao, X. D. J. Heterocycl. Chem. 2009, 46, 563.
(e) Chen, D. S.; Zhou, Y. J.; Li, Y. L.; Yao, C. S.; Wang X. S. Comb. Chem. High Throughput. Screening 2013, 16, 550.
(f) Xun, Z.; Feng, X.; Wang, J.; Shi, D.; Huang, Z. Chin. J. Chem. 2016, 34, 696.
[4] Walker, M. J. A. Biochem. Pharmacol. 2015, 98, 335.
[5] Cifuentes, F.; Paredes, A.; Palacios, J.; Munoz, F.; Carvajal, L.; Nwokocha, C. R.; Morales, G. J. Ethnopharmacol. 2016, 179, 367.
[6] Kargbo, R; Takahashi, Y; Bhor, S; Cook, G. R.; Lloyd-Jones, G. C.; Shepperson, I. R. J. Am. Chem. Soc. 2007, 129, 3846.
[7] Stasiak, J.; Koba, M.; Baczek, T.; Bucinski, A. Med. Chem. 2015, 11, 432.
[8] Tu, S.; Zhang, Y.; Zhang, J.; Jiang, B.; Jia, R.; Zhang, J.; Ji, S. Synlett 2006, 2785.
[9] Kozlov, N. G.; Bondarev, S. L.; Kadutskii, A. P.; Basalaeva, L. I.; Pashkovskii, F. S. Russ. J. Org. Chem. 2008, 44, 1031.
[10] Shi, C.; Wang, J.; Chen, H.; Shi, D. J. Comb. Chem. 2010, 12, 430.
[11] Aillerie, A.; de Talancé, V. L.; Moncomble, A.; Bousquet, T.; Pélinski, L. Org. Lett. 2014, 16, 2982.
[12] Tu, S.; Wu, S.; Yan, S.; Hao, W.; Zhang, X.; Cao, X.; Han, Z.; Jiang, B.; Shi, F.; Xia, M.; Zhou, J. J. Comb. Chem. 2009, 11, 239.
[13] Shi, F.; Zhou, D.; Tu, S.; Shao, Q.; Li, C.; Cao, L. J. Heterocycl. Chem. 2008, 45, 1065.
[14] Shi, D.; Li, Y.; Shi, C.; Wang, H. Acta Chim. Sinica 2009, 67, 645.
[15] Kamal, A.; Tamboli, J. R.; Nayak, V. L.; Adil, S. F.; Vishnuvardhan, M. V. P. S.; Ramakrishna, S. Bioorg. Med. Chem. 2014, 22, 2714.
[16] Sandaroos, R.; Damavandi, S.; Molaei, H. R. Res. Chem. Intermed. 2015, 41, 1517.
[17] Vilches-HerreraIngo, M.; de SouzaAlexander, K.; Vyacheslav, V.; Sosnovskikh, Y.; Iaroshenko, V. O. ACS Comb. Sci. 2012, 14, 434.

无催化条件下三组分一锅法合成呋喃并吡啶并喹喔啉衍生物

One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	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.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[14]	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.
[15]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.