Ruthenium-Catalyzed One-Pot Synthesis of Quinolines from Nitroarenes and Trialkylamines

doi:10.6023/cjoc1202231

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (9): 1725-1731.DOI: 10.6023/cjoc1202231 Previous Articles Next Articles

Notes

钌催化芳香硝基化合物和脂肪三级胺反应一锅法合成喹啉衍生物

杨辉琼^a,b, 谌儒^b, 邓国军^b

a 湖南工程学院化学化工学院湘潭 411104;
b 湘潭大学化学学院湘潭 411105

收稿日期:2012-02-23 修回日期:2012-06-01 发布日期:2012-05-16
通讯作者: 杨辉琼 E-mail:yanghuiqiong2996@126.com
基金资助:
国家自然科学基金(No.20902076)资助项目

Ruthenium-Catalyzed One-Pot Synthesis of Quinolines from Nitroarenes and Trialkylamines

Yang Huiqiong^a,b, Chen Ru^b, Deng Guojun^b

a College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104;
b College of Chemistry, Xiangtan University, Xiangtan 411105

Received:2012-02-23 Revised:2012-06-01 Published:2012-05-16
Supported by:
Project supported by the National Natural Science Foundation of China (No.20902076)

A series of quinolines were synthesized in moderate yields by one-pot reaction of nitroarenes and trialkylamines in the presence of a catalytic amount of ruthenium trichloride catalyst together with tricyclohexylphosphonium tetrafluoroborate ligand. This method is convenient without extra reductant, and nitroarenes are cheap and highly available. The structures of the products were characterized by IR,¹H NMR,¹³C NMR, MS techniques and elemental analysis.

Key words: C—N bond formation, one-pot synthesis, quinolines, ruthenium catalyst, nitroarenes, trialkylamines

Cite this article

Yang Huiqiong, Chen Ru, Deng Guojun. Ruthenium-Catalyzed One-Pot Synthesis of Quinolines from Nitroarenes and Trialkylamines[J]. Chin. J. Org. Chem., 2012, 32(9): 1725-1731.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Wei, X. L.; Su, R. B. Bull. Acad. Millitry Med. Sci. 2002, 26, 228 (in Chinese). (魏晓莉, 苏瑞斌, 军事医学科学院院刊, 2002, 26, 228.)

(b) Mikhailitsyn, F. S.; Kozyreva, N. P.; Rabinovich, S. A.; Maksakovskaya, Y. V.; Kulikovskaya, I. M.; Dadasheva, N. R.; Lebedeva, M. N.; Bekhli, A. F.; Lychko, N. D.; Uvarova, N. A. Med. Parazitol. Parazit. Bolezni 1992, 1, 50.

[2] Via, L. D.; Gia, O.; Gasparotto, V.; Ferlin, M. G. Eur. J. Med. Chem. 2008, 43, 429.

[3] Prescott, T. A. K.; Sadler, I. H.; Kiapranis, R. J. Ethnopharmacol. 2007, 109, 289.

[4] Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1979, 44, 3985.

[5] (a) Wu, Y. C.; Liu, L.; Li, H. J.; Wang, D.; Chen,Y. J. J. Org. Chem. 2006, 71, 6592.

(b) Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668

[6] Jutz, C.; Wagner, R. M. Angew. Chem., Int. Ed. Engl. 1972, 11, 315.

[7] (a) Kaslow, C. E.; Summers, R. M. J. Org. Chem. 1955, 20, 1738.

(b) Hause, C. R.; Murray, J. G. J. Am. Chem. Soc. 1955, 77, 2851.

[8] (a) Yang, D. Q.; Lü, F.; Guo, W. Chin. J. Org. Chem. 2004, 24, 366 (in Chinese).(杨定乔, 吕芬, 郭维, 有机化学, 2004, 24, 366.)

(b) Wu, L. H.; Yang, D. Q. Chin. J. Org. Chem. 2010, 30, 1180 (in Chinese).(吴利欢, 杨定乔, 有机化学, 2010, 30, 1180.)

[9] Shindoh, N.; Tokuyama, H.; Takemoto,Y.; Takasu, K. J. Org. Chem. 2008, 73, 7451.

[10] (a) Zhang, W. W.; Wang, X. S.; Li, Q.; Yao, C. S.; Tu, S. J. Chin. J. Org. Chem. 2008, 28, 881 (in Chinese).(张梅梅, 王香善, 李庆, 姚昌盛, 屠树江, 有机化学, 2008, 28, 881.)

(b) Mali, J. R.; Pratap, U. R.; Jawale, D. V.; Mane, R. A. Tetrahedron Lett. 2010, 51, 3980.

[11] (a) Wang, H. S.; Zeng, J. E. Chin. J. Org. Chem. 2010, 30, 1072 (in Chinese).(王宏社, 曾君娥, 有机化学, 2010, 30, 1072.)

(b) Hollmann, D.; Bahn, S.; Tillack, A.; Beller, M. Chem. Commun. 2008, 44, 3199.

(c) Lubinu, M.; Luca, L.; Giacomelli, G.; Porcheddu, A. Chem. Eur. J. 2011, 17, 82.

(d) Lang, X. J.; Ji, H. W.; Chen, C. C.; Ma, W. H.; Zhao, J. C. Angew. Chem., Int. Ed. 2011, 50, 3934.

(e) Liu, L. H.; Zhang, S. Y.; Fu, X. F.; Yan, C. H. Chem. Commun. 2011, 47, 10148.

(f) Saidi, O.; Blacker A.; Farah, M.; Marsdon, S.; Williams, J. Angew. Chem., Int. Ed. Engl. 2009, 48, 7375.

[12] (a) Feng, C.; Liu, Y.; Peng, S. M.; Shuai, Q.; Deng, G. J.; Li, C. J. Org. Lett. 2010, 12, 4888.

(b) Liu, Y.; Chen, W.; Feng, C.; Deng, G. J. Chem. Asian J. 2011, 6, 1142.

(c) Xiao, F. H.; Liu, Y.; Tang, C. L.; Deng, G. J. Org. Lett. 2012, 14, 984.

[13] Watanabe, Y.; Shim, S. C.; Mitsudo, T. Bull. Chem. Soc. Jpn. 1981, 54, 3460.

[14] Nakajima, T.; Inada, T.; Igarashi, T.; Sekioka, T.; Shimizu, I. Bull. Chem. Soc. Jpn. 2006, 79, 1941.

[15] Case, J. J. Chem. Eng. Data 1968, 13, 568.

[16] Yamamoto, I.; Furukawa, T.; Nakajima, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1 1976, 1597.

[17] Wang, D.; Wang, X.; Wang, D.; Lu, S.; Zhou, Y.; Li, Y. J. Org. Chem. 2009, 74, 2780.

[18] Cho, C.; Lee, N.; Kim, T.; Shim, S. J. Heterocycl. Chem. 2004, 41, 423.

[19] (a) Basu, A.; Bhaduri, S.; Sharma, K.; Jones, P. G. J. Chem. Soc., Chem. Commun. 1987, 1126.

(b) Wang, G. Z.; Bäckvall, J. E. J. Chem. Soc., Chem. Commun. 1992, 980.

[20] Kharasch M. S.; Richlin, I.; Mayo, F. R. J. Am. Chem. Soc. 1940, 62, 494.

[21] Watanabe, Y.; Tsuji, Y.; Ohsugi, Y.; Shida, J. Bull. Chem. Soc. Jpn. 1983, 56, 2452.

钌催化芳香硝基化合物和脂肪三级胺反应一锅法合成喹啉衍生物

Ruthenium-Catalyzed One-Pot Synthesis of Quinolines from Nitroarenes and Trialkylamines

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Changyuan Du, Yucai Tang, Jinglin Duan, Biyu Yang, Yupeng He, Qian Zhou, Xuewen Liu. Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4268-4276.
[2]	Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang. PPh₃-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3997-4002.
[3]	Keli Wang, Jing Huang, Wei Liu, Zhilin Wu, Xianyong Yu, Jun Jiang, Weimin He. Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2527-2534.
[4]	Wensheng Zhang, Yan Li, Haiyan Cui, Xiaoli Su, Supeng Xu. One-Pot Synthesis of N-Substituted Isoindolin-1-ones via Reductive Amination/Lactamization of Methyl 2-Formylbenzoate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2456-2461.
[5]	Tao Li, Yi Liu, Xue Bai, Zunjun Zhou, Peng Zuo, Miaofeng Ma, Chong-Min Zhong, Ya-Jie Zuo. Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1713-1721.
[6]	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.
[7]	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.
[8]	Hongyan Shi, Ying Zhong, Zhigang Zhao. Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 677-687.
[9]	Jianing Che, Tao Song, Xianchi Gao, Yong Yang. Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 276-283.
[10]	Fang Xiaolong, Duan Ning, Zhang Min, Li Bin. Advances for Ruthenium Catalysts with Metal-Ligand Cooperation for Hydrogenation of Oxalates into Ethylene Glycol [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2692-2701.
[11]	Liu Zilin, Zhang Xiaojie, Zhang Heng, Jiang Hui, Zhao Xuemei, Shi Linlin, Zhu Xinju, Hao Xinqi, Song Maoping. Phathalocyanine Metal Complexes (M=Fe, Co, and Cu) Catalyzed Aerobic Oxidation of 2-Amino-benzyl Alcohols to Access Quinazolines and Quinolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2755-2763.
[12]	He Shuwang, Yan Shiqiang, Guo Wei, Zhai Guangxi, Zhang Wei. One-Pot Synthesis of Amino Alcohols from Styrenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2094-2098.
[13]	Lan Jin, Xie Zongbo, Yang Jiangnan, Meng Jia, Liu Yishuai, Le Zhanggao. One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1331-1336.
[14]	Wang Xin, Li Guofeng, Sun Kai, Zhang Bing. Peroxide-Induced Radical Relay Carbocyclization towards Polycyclic Benzimidazole[2,1-a]isoquinolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 913-921.
[15]	Wan Linxi, Gao Feng, Chen Wei, Zhou Xianli. One-Pot Synthesis of 2-((2-Aminobenzoyl)amino)benzoic Acid Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2270-2276.