One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds

doi:10.6023/cjoc201612038

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1433-1442.DOI: 10.6023/cjoc201612038 Previous Articles Next Articles

Articles

一锅法合成多取代色酮并双环吡啶类化合物

陈亮, 王保取, 赵宇澄, 严胜骄, 林军

云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明 650091

收稿日期:2016-12-12 修回日期:2017-01-21 发布日期:2017-02-20
通讯作者: 严胜骄,林军 E-mail:yansj@ynu.edu.cn;linjun@ynu.edu.cn
基金资助:
国家自然科学基金（Nos.U1202221，21362042，21262042，21662042）、云南省后备人才（No.2012HB001）、云南大学青年英才计划（No.XT412003）资助项目.

One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds

Chen Liang, Wang Baoqu, Zhao Yucheng, Yan Shengjiao, Lin Jun

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science andTechnology, Yunnan University, Kunming 650091

Received:2016-12-12 Revised:2017-01-21 Published:2017-02-20
Contact: 10.6023/cjoc201612038 E-mail:yansj@ynu.edu.cn;linjun@ynu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. U1202221, 21362042, 21262042, 21662042), the Talent Found in Yunnan Province (No. 2012HB001), and the Excellent Young Talents of Yunnan University (No. XT412003).

1. One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds.PDF(473KB)

Abstract

A concise and environment friendly route for the synthesis of multisubstituted chromone-fused bicyclic pyridine compounds via one-step reaction of chromone-3-carboxaldehyde 1 and N-benzyl nitro ketene aminals (NBNKAs, 2) in ethanol media has been developed. The targeted compounds 3 can efficiently obtain by filter without extra post-treatment. The reaction is particularly attractive due to following features: low-cost and biocompatibility solvent, mild temperature, atom economy, high yields, and potential biological activity.

Key words: environment friendly, atom economy, catalyst-free, bicyclic pyridine, neonicotinoids

Cite this article

Chen Liang, Wang Baoqu, Zhao Yucheng, Yan Shengjiao, Lin Jun. One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds[J]. Chin. J. Org. Chem., 2017, 37(6): 1433-1442.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Hunt, A. J.; Sin, E. H. K.; Marriott, R.; Clark, J. H. CHemSusChem 2010, 3, 306.
[2] Agana, B. A.; Reeve, D.; Orbell, J. D. J Environ. Manage. 2013, 114, 445.
[3] Marr, P. C.; Marr, A. C. Green Chem. 2016, 18, 105.
[4] Marteel-Parrish, A. E. J. Chem. Educ. 2014, 91, 1084.
[5] Trost, B. M. Science 1991, 254, 1471.
[6] Misono, M. Yuki Gosei Kagaku Kyokaishi 2003, 61, 406.
[7] Hartman, G. J.; Jin, Q. Z.; Collins, G. J.; Lee, K. N.; Ho, C. T.; Chang, S. S. J. Agric. Food Chem. 1983, 31, 1030.
[8] Ren, T.; Liu, W.; Xue, Q.; Wang, H. Lubr. Sci. 1993, 5, 205.
[9] Ueda, Y.; Connolly, T. P.; Kadow, J. F.; Meanwell, N. A.; Wang, T.; Chen, C.-P. H.; Yeung, K.-S.; Zhang, Z.; Leahy, D. K.; Pack, S. K.; Soundararajan, N.; Sirard, P.; Levesque, K.; Thoraval, D. US 20050209246, 2005[Chem. Abstr. 2005, 143, 306343].
[10] Garuti, L.; Roberti, M.; Pizzirani, D. Mini-Rev. Med. Chem. 2007, 7, 481.
[11] Schultz, C.; Link, A.; Leost, M.; Zaharevitz, D. W.; Gussio, R.; Sausville, E. A.; Meijer, L.; Kunick, C. J. Med. Chem. 1999, 42, 2909.
[12] Pluta, K.; Morak-Mlodawska, B.; Jelen, M. Eur. J. Med. Chem. 2011, 46, 3179.
[13] Sujatha, K.; Shanmugam, P.; Perumal, P. T.; Muralidharan, D.; Rajendran, M. Bioorg. Med. Chem. Lett. 2006, 16, 4893.
[14] Helal, C. J.; Kang, Z.; Hou, X.; Pandit, J.; Chappie, T. A.; Humphrey, J. M.; Marr, E. S.; Fennell, K. F.; Chenard, L. K.; Fox, C.; Schmidt, C. J.; Williams, R. D.; Chapin, D. S.; Siuciak, J.; Lebel, L.; Menniti, F.; Cianfrogna, J.; Fonseca, K. R.; Nelson, F. R.; O'Connor, R.; MacDougall, M.; McDowell, L.; Liras, S. J. Med. Chem. 2011, 54, 4536.
[15] Kim, I. Y.; Kim, S. H. KR 2016006050, 2016[Chem. Abstr. 2016, 164, 225869].
[16] Lhassani, M.; Chavignon, O.; Chezal, J.-M.; Teulade, J.-C.; Chapat, J.-P.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Gueiffier, A. Eur. J. Med. Chem. 1999, 34, 271.
[17] Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernandez, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290.
[18] Mizushige, K.; Ueda, T.; Yukiiri, K.; Suzuki, H. Cardiovasc. Drug Rev. 2002, 20, 163.
[19] Ankley, G. T.; Kahl, M. D.; Jensen, K. M.; Hornung, M. W.; Korte, J. J.; Makynen, E. A.; Leino, R. L. Toxicol. Sci. 2002, 67, 121.
[20] Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615.
[21] Bai, D.; Lummis, S. C. R.; Leicht, W.; Breer, H.; Sattelle, D. B. Pestic. Sci. 1991, 33, 197.
[22] Feng, X.-G.; Liu, X.-W.; Han, Z.-L.; Guan, L.-T.; Xu, L.-Z. J. Qingdao Univ. Sci. Technol., Nat. Sci. Ed. 2012, 33, 381.
[23] Li, J.; Huang, T.; Li, L.; Ding, T.; Zhu, H.; Yang, B.; Ye, Q.; Gan, J. J. Agric. Food Chem. 2016, 64, 8109.
[24] Tomizawa, M.; Casida, J. E. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 247.
[25] Bao, H.; Shao, X.; Zhang, Y.; Deng, Y.; Xu, X.; Liu, Z.; Li, Z. J. Agric. Food Chem. 2016, 64, 5148.
[26] Lu, S.; Zhuang, Y.; Wu, N.; Feng, Y.; Cheng, J.; Li, Z.; Chen, J.; Yuan, J.; Xu, X. J. Agric. Food Chem. 2013, 61, 10858.
[27] Shao, X.; Xu, Z.; Zhao, X.; Xu, X.; Tao, L.; Li, Z.; Qian, X. J. Agric. Food Chem. 2010, 58, 2690.
[28] (a) Huang, Z.; Wang, M. Heterocycles 1994, 37, 1233.
(b) Kong, L.; Yang, R.; Du, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2016, 36, 2437 (in Chinese). (孔令斌, 杨瑞霞, 杜璇璇, 严胜骄, 林军, 有机化学, 2016, 36, 2437.)
(c) Peng, M.; Yang, R.; Liu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2015, 35, 1754 (in Chinese). (彭美阳, 杨瑞霞, 刘昔敏, 严胜骄, 林军, 有机化学, 2015, 35, 1754.)
[29] (a) Chen, X.-B.; Liu, Z.-C.; Lin, X.-R.; Huang, R.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 2391.
(b) Luo, D.; Cui, S.; Hu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2017, 37, 166 (in Chinese). (罗大云, 崔时胜, 胡兴梅, 林军, 严胜骄, 有机化学, 2017, 37, 166.)
[30] Yu, F.-C.; Huang, R.; Ni, H.; Fan, J.; Yan, S.-J.; Lin, J. Green Chem. 2013, 15, 453.
[31] Chen, X.-B.; Liu, Z.-C.; Yang, L.-F.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 1155.
[32] Xiao, X.; Wang, X.; Gui, X.; Chen, L.; Huang, B. Chem. Biodiversity 2016, 11, 1427.
[33] Mir, S. A. Int. J. PharmTech Res. 2016, 9, 70.
[34] (a) Ding, Z.-W.; Tan, Q.-T.; Liu, B.-X.; Xu, K.; Xu, B. Acta Chim. Sinica 2015, 73, 1302 (in Chinese). (丁正伟, 谭启涛, 刘秉新, 张可, 许斌, 化学学报, 2015, 73, 1302.)
(b) Zhao, J.-B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235 (in Chinese). (赵金钵, 张前, 化学学报, 2015, 73, 1235.)
[35] Alizadeh, A.; Bayat, F.; Zhu, Z. Res. Chem. Intermed. 2016, 42, 5927.
[36] Yaqub, M.; Perveen, R.; Shafiq, Z.; Pervez, H.; Tahir, M. N. Synlett 2012, 23, 1755.
[37] Nishiwaki, H.; Nakagawa, Y.; Takeda, D. Y.; Okazawa, A.; Akamatsu, M.; Miyagawa, H.; Ueno, T.; Nishimura, K. Pest Manage. Sci. 2000, 56, 875.

一锅法合成多取代色酮并双环吡啶类化合物

One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[2]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[3]	Haojie Ma, Fengyuan Zhou, Jinlei Liu, Bo Han, Hua Yang, Yuqi Zhang, Jijiang Wang. Construction of Substituted N-Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1843-1848.
[4]	Xiaoting Wu, Feng Zhao, Xiaochen Ji, Huawen Huang. Visible Light-Assisted Photocatalyst-Free Tandem Sulfonylation/ Cyclization for the Synthesis of Oxindoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4323-4331.
[5]	Xiaoshuang Ji, Rong Fu, Shuliang Wang, Wenjuan Hao, Bo Jiang. Visible-Light-Driven Photocatalytic Kharasch Reaction of Phenol/ Arylamine-Linked 1,6-Enynes with Perhalogenated Methane [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4282-4291.
[6]	Haojie Ma, Xiaoqiang Zhou, Bo Han, Ran Li, Xueyan Hou, Xingyue Ji, Yuqi Zhang, Guosheng Huang, Jijiang Wang. A Catalyst-Free One-Pot Protocol for the Construction of Substituted Sulfonyl Pyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3710-3716.
[7]	Qinghan Li, Ruiqiang Luo, Chuan Wu, Hongliu Xiao, Shaopeng Guo, Zhihao Zhang, Zheyao Huang, Lin Zhou. Research Progress of Cross-Coupling Reactions of Alkylaluminums with Electrophiles Reagents [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1489-1497.
[8]	Yujuan Xiao, Yang Yang, Fan Zhang, Yadong Feng, Xiuling Cui. UV-Light-Initiated Construction of Indenones through Cyclization of Aryl Aldehydes or Aryl Ketones with Alkynes Avoiding Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4808-4814.
[9]	Ding Yuxin, Ma Yongmin, Chen Jing. Novel Three-Component Annulation for the Synthesis of 2,4,6-Triaryl-pyrimidines under Solvent-Free and Catalyst-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4357-4363.
[10]	Wang Bin, Ye Wenbo, Yan Zicong, Wan Changfeng, Hou Haoqing, Wang Zhiyong. A New Catalyst-Free Synthesis of 2,3-Dicarboxylic Ester Quinoline Derivatives [J]. Chin. J. Org. Chem., 2018, 38(2): 504-508.
[11]	Yan Yizhe, Cui Chang, Li Zheng. Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine [J]. Chin. J. Org. Chem., 2018, 38(10): 2501-2518.
[12]	Zhang Wenfeng, Xu Zhaohui, Tu Yuanhong, Liao Chuanwen. Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water [J]. Chin. J. Org. Chem., 2017, 37(9): 2449-2453.
[13]	Hao Wenyan, Wang Yuyun, Liu Yunyun. Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines [J]. Chin. J. Org. Chem., 2017, 37(12): 3198-3203.
[14]	Wang Baoqu, Kong Lingbin, Luo Qin, Lin Jun, Yan Shengjiao. One-Step Synthesis of Isoquinolinone Compounds [J]. Chin. J. Org. Chem., 2017, 37(11): 2972-2977.
[15]	Li Lingjie, Zhang Jing, Tang Yu, Xu Kaitian, Zhang Yuanming. Catalyst-Free One-Pot Synthesis of 4-Substituted Quinazolines [J]. Chin. J. Org. Chem., 2017, 37(10): 2711-2716.