Synthesis of 1,2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride

doi:10.6023/cjoc202004015

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3446-3451.DOI: 10.6023/cjoc202004015 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

氰基硼氢化钠还原喹啉合成1,2-二氢喹啉

徐徐清风^a, 黄显韵^b, 张霄^a, 游书力^a,b

a 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032;
b 华东理工大学药学院上海 200237

收稿日期:2020-04-10 修回日期:2020-05-09 发布日期:2020-05-15
通讯作者: 游书力 E-mail:slyou@sioc.ac.cn
基金资助:
国家科技计划（No.2016YFA0202900）和国家自然科学基金（No.21821002）资助项目.

Synthesis of 1,2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride

Xu-Xu Qing-Feng^a, Huang Xian-Yun^b, Zhang Xiao^a, You Shu-Li^a,b

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
b School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Received:2020-04-10 Revised:2020-05-09 Published:2020-05-15
Supported by:
Project supported by the Ministry of Science and Technology of China (No. 2016YFA0202900) and the National Natural Science Foundation of China (No. 21821002).

1. 203446S.pdf(773KB)

Abstract

An efficient conversion of quinolines to 1,2-dihydroquinolines (50%~96% yield) was developed via the modification of the known methods. It was found that using sodium cyanoborohydride as a reductant would overcome the low conversion often encountered in previous studies. A series of N-alkoxycarbonyl-1,2-dihydroquinolines were obtained through reduction of activated quinolium salts. Notably, with the exception of the 3-and 4-substituted substrates, a mixture of 1,2-dihydro-quinolines and the over reduced tetrahydroquinolines was obtained with the ratio over 4:1. Besides, compared to the established methods, an easy operation without using large excess of chloroformate further enhances practicability of the methodology.

Key words: quinoline, 1,2-dihydroquinoline, dearomatization, sodium cyanoborohydride

Cite this article

Xu-Xu Qing-Feng, Huang Xian-Yun, Zhang Xiao, You Shu-Li. Synthesis of 1,2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3446-3451.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Belleau, B.; Martel, R. R.; Lacasse, G.; Menard, M.; Weinberg, N. L.; Perron, Y. G. J. Am. Chem. Soc. 1968, 90, 823.
(b) Dillard, R. D.; Pavey, D. E.; Benslay, D. N. J. Med. Chem. 1973, 16, 251.
(c) Takahashi, H.; Bekkali, Y.; Capolino, A. J.; Gilmore, T.; Goldrick, S. E.; Nelson, R. M.; Trenzio, D.; Wang, J.; Zuvela-Jelaska, L.; Proudfoot, J.; Nabozny, G.; Thomson, D. Bioorg. Med. Chem. Lett. 2006, 16, 1549.
(d) Victor, N. J.; Sakthivel, R.; Muraleedharan, K. M.; Karunagaran, D. ChemMedChem 2013, 8, 1623.
(e) Duggirala, S.; Napoleon, J. V.; Nankar, R. P.; Adeeba, V. S.; Manheri, M. K.; Doble, M. Eur. J. Med. Chem. 2016, 123, 557.
[2] (a) Jean-Gérard, L.; Macé, F.; Ngo, A. N.; Pauvert, M.; Dentel, H.; Evain, M.; Collet, S.; Guingant, A. Eur. J. Org. Chem. 2012, 2012, 4240.
(b) Ren, X.; Li, G.; Huang, J.; Wang, W.; Zhang, Y.; Xing, G.; Gao, C.; Zhao, G.; Zhao, J.; Tang, Z. Org. Lett. 2017, 19, 58.
(c) Graham, T. J. A.; Shields, J. D.; Doyle, A. G. Chem. Sci. 2011, 2, 980.
(d) Kodama, T.; Moquist, P. N.; Schaus, S. E. Org. Lett. 2011, 13, 6316.
(e) Sun, S.; Mao, Y.; Lou, H.; Liu, L. Chem. Commun. 2015, 51, 10691.
(f) Volla, C. M. R.; Fava, E.; Atodiresei, I.; Rueping, M. Chem. Commun. 2015, 51, 15788.
(g) Berti, F.; Malossi, F.; Marchetti, F.; Pineschi, M. Chem. Commun. 2015, 51, 13694.
(h) Liu, Z.; Zhao, R.; He, N.; Li, W. Chin. J. Org. Chem. 2018, 38, 1261(in Chinese). (刘子强, 赵冉, 贺妮, 李伟, 有机化学, 2018, 38, 1261.)
[3] (a) Li, G.; Liu, H.; Wang, Y.; Zhang, S.; Lai, S.; Tang, L.; Zhao, J.; Tang, Z. Chem. Commun. 2016, 52, 2304.
(b) Kubota, K.; Watanabe, Y.; Ito, H. Adv. Synth. Catal. 2016, 358, 2379.
(c) Kong, D.; Han, S.; Wang, R.; Li, M.; Zi, G.; Hou, G. Chem. Sci. 2017, 8, 4558.
(d) Kong, D.; Han, S.; Zi, G.; Hou, G.; Zhang, J. J. Org. Chem. 2018, 83, 1924.
(e) Xu-Xu, Q.-F.; Zhang, X.; You, S.-L. Org. Lett. 2019, 21, 5357.
(f) Wedek, V.; Lommel, R. V.; Daniliuc, C. G.; Proft, F. D.; Hennecke, U. Angew. Chem. Int. Ed. 2019, 58, 9239.
(g) Xu-Xu, Q.-F.; Zhang, X.; You, S.-L. Org. Lett. 2020, 22, 1530.
[4] For a related reaction by using 1, 2-dihydropyridines, see:Kubota, K.; Watanabe, Y.; Hayama, K.; Ito, H. J. Am. Chem. Soc. 2016, 138, 4338.
[5] (a) Tiwari, V. K.; Pawar, G. G.; Das, R.; Adhikary, A.; Kapur, M. Org. Lett. 2013, 15, 3310.
(b) Das, R.; Khot, N. P.; Deshpande, A. S.; Kapur, M. Chem. Eur. J. 2020, 26, 927.
[6] Pang, M.; Chen, J.-Y.; Zhang, S.; Liao, R.-Z.; Tung, C.-H.; Wang, W. Nat. Commun. 2020, 11, 1249.
[7] (a) Luo, Y.; Li, Z.; Li, C.-J. Org. Lett. 2005, 7, 2675.
(b) Liu, X.; Lu, Y. Org. Biomol. Chem. 2010, 8, 4063.
(c) Zhu, C.; Ma, S. Angew. Chem. Int. Ed. 2014, 53, 13532.
(d) Luo, Q.; Xie, Y.; Chen, Z.; Yan, S.; Deng, W.; Liu, Y.; Wang, L. Chin. J. Org. Chem. 2014, 34, 2537(in Chinese). (罗倩, 谢永新, 陈朝阳, 闫世友, 邓文叶, 刘义, 王璐璐, 有机化学, 2014, 34, 2537.)
(e) Ding, D.; Mou, T.; Feng, M.; Jiang, X. J. Am. Chem. Soc. 2016, 138, 5218.
(f) Kuppusamy, R.; Santhoshkumar, R.; Boobalan, R.; Wu, H.-R.; Cheng, C.-H. ACS Catal. 2018, 8, 1880.
(g) Wang, G.; Huang, H.; Guo, W.; Qian, C.; Sun, J. Angew. Chem. Int. Ed. 2020, 59, 11245.
[8] For selected reviews, see: (a) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.
(b) Luo, Y.-E.; He, Y.-M.; Fan, Q.-H. Chem. Rec. 2016, 16, 2697.
(c) Giustra, Z. X.; Ishibashi, J. S. A.; Liu, S.-Y. Coord. Chem. Rev. 2016, 314, 134.
(d) Meng, W.; Feng, X.; Du, H. Acc. Chem. Res. 2018, 51, 191.
(e) Meng, W.; Feng, X.; Du, H. Chin. J. Chem. 2020, 38, 625. For recent examples, see:
(f) Cai, X.-F.; Huang, W.-X.; Chen, Z.-P.; Zhou, Y.-G. Chem. Commun. 2014, 50, 9588.
(g) Li, B.; Xu, C.; He, Y.-M.; Deng, G.-J.; Fan, Q.-H. Chin. J. Chem. 2018, 36, 1169.
(h) Chen, Y.; He, Y.-M.; Zhang, S.; Miao, T.; Fan, Q.-H. Angew. Chem. Int. Ed. 2019, 58, 3809.
(i) Hu, X.-H.; Hu, X.-P. Org. Lett. 2019, 21, 10003.
(j) Liu, Y.; Chen, F.; He, Y.-M.; Li, C.; Fan, Q.-H. Org. Biomol. Chem. 2019, 17, 5099.
(k) Chen, Y.; Pan, Y.; He, Y.-M.; Fan, Q.-H. Angew. Chem. Int. Ed. 2019, 58, 16831.
(l) Li, X.; Tian, J.-J.; Liu, N.; Tu, X.-S.; Zeng, N.-N.; Wang, X.-C. Angew. Chem. Int. Ed. 2019, 58, 4664.
(m) Tao, L.; Ren, Y.; Li, C.; Li, H.; Chen, X.; Liu, L.; Yang, Q. ACS Catal. 2020, 10, 1783.
(n) Wang, L.-R.; Chang, D.; Feng, Y.; He, Y.-M.; Deng, G.-J.; Fan, Q.-H. Org. Lett. 2020, 22, 2251.
[9] For selected reviews, see: (a) Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498. For recent examples, see:
(b) Cai, X.-F.; Guo, R.-N.; Feng, G.-S.; Wu, B.; Zhou, Y.-G. Org. Lett. 2014, 16, 2680.
(c) Cai, X.-F.; Guo, R.-N.; Chen, M.-W.; Shi, L.; Zhou, Y.-G. Chem. Eur. J. 2014, 20, 7245.
(d) Guo, R.-N.; Chen, Z.-P.; Cai, X.-F.; Zhou, Y.-G. Synthesis 2014, 46, 2751.
(e) Wang, J.; Chen, M.-W.; Ji, Y.; Hu, S.-B.; Zhou, Y.-G. J. Am. Chem. Soc. 2016, 138, 10413.
(f) Aillerie, A.; Lemau de Talencé, V.; Dumont, C.; Pellegrini, S.; Capet, F.; Bousquet, T.; Pélinski, L. New J. Chem. 2016, 40, 9034.
(g) Zhang, J.-F.; Zhong, R.; Zhou, Q.; Hong, X.; Huang, S.; Cui, H.-Z.; Hou, X.-F. ChemCatChem 2017, 9, 2496.
(h) Mitra, R.; Zhu, H.; Grimme S.; Niemeyer, J. Angew. Chem. Int. Ed. 2017, 56, 11456.
(i) Qiao, X.; El-Shahat, M.; Ullah, B.; Bao, Z.; Xing, H.; Xiao, L.; Ren, Q.; Zhang, Z. Tetrahedron Lett. 2017, 58, 2050.
(j) Han, Y.; Wang, Z.; Xu, R.; Zhang, W.; Chen, W.; Zheng, L.; Zhang, J.; Luo, J.; Wu, K.; Zhu, Y.; Chen, C.; Peng, Q.; Liu, Q.; Hu, P.; Wang, D.; Li, Y. Angew. Chem. Int. Ed. 2018, 57, 11262.
(k) Chen, X.; Chen, J.; Bao, Z.; Yang, Q.; Yang, Y.; Ren, Q.; Zhang, Z. Chin. J. Org. Chem. 2019, 39, 1681(in Chinese). (陈晓玲, 陈静雯, 鲍宗必, 杨启炜, 杨亦文, 任其龙, 张治国, 有机化学, 2019, 39, 1681.)
[10] For a review, see: (a) Park, S.; Chang, S. Angew. Chem. Int. Ed. 2017, 56, 7720. For selected examples, see:
(b) Voutchkova, A. M.; Gnanamgari, D.; Jakobsche, C. E.; Butler, C.; Miller, S. J.; Parr, J.; Crabtree, R. H. J. Organomet. Chem. 2008, 693, 1815.
(c) Arrowsmith, M.; Hill, M. S.; Hadlington, T.; Kociok-Köhn, G.; Weetman, C. Organometallics 2011, 30, 5556.
(d) Dudnik, A. S.; Weidner, V. L.; Motta, A.; Delferro, M.; Marks, T. J. Nat. Chem. 2014, 6, 1100.
(e) Intemann, J,; Bauer, H.; Pahl, J.; Maron, L.; Harder, S. Chem. Eur. J. 2015, 21, 11452.
(f) Jeong, J.; Park, S.; Chang, S. Chem. Sci. 2016, 7, 5362.
(g) Liu, Z.-Y.; Wen, Z.-H.; Wang, X.-C. Angew. Chem. Int. Ed. 2017, 56, 5817.
(h) Zhang, F.; Song, H.; Zhuang, X.; Tung, C.-H.; Wang, W. J. Am. Chem. Soc. 2017, 139, 17775.
(i) Rao, B.; Chong, C. C.; Kinjo, R. J. Am. Chem. Soc. 2018, 140, 652.
[11] Too, P. C.; Chan, G. H.; Tnay, Y. L.; Hirao, H.; Chiba, S. Angew. Chem. Int. Ed. 2016, 55, 3719.
[12] Blackburn, B. K.; Frysinger, J. F.; Minter, D. E. Tetrahedron Lett. 1984, 25, 4913.

[1]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[2]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[3]	Yue Zhu, Lu Chen, Jing Zhao, Qingrong Sun, Weiqing Yang, Haiyan Fu, Menglin Ma. Synthesis of Quinoline Derivatives by Friedländer Reaction Catalyzed by Ruthenium Complexes of Substituted 8-Hydroxyquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2528-2542.
[4]	Weina Tian, Liang Xu, Yu Wei, Pengfei Li. Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1792-1798.
[5]	Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia. Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1875-1882.
[6]	Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.
[7]	Jianfei Gao, Shunyi Li, Yulong He, Yingxia Li, Heyao Wang, Erfang Huang, Chun Hu. Design, Synthesis and Biological Evaluation of FABP4/5 Inhibitors Based on Quinoline Scaffold [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 636-645.
[8]	Huan Xu, Hongfei Wu, Xiaoming Zhang, Xingxing Lu, Tengda Sun, Yue Qi, Yufan Lin, Xinling Yang, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 725-733.
[9]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[10]	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.
[11]	Junxiu Liang, Yazhou Liu, Amu Wang, Yanchao Wu, Xiaofeng Ma, Huijing Li. Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3888-3899.
[12]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[13]	Zhi-You Huang, Ning Zhang, Han-Wen Zuo, Xu-Qi Zeng, Han Liu. Design, Synthesis and Seed Germination Inhibition Activity of Quinoline-6-sulfonamide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2947-2953.
[14]	Haoyang Liu, Shuangshuang Sun, Xianli Ma, Yanyan Chen, Yanli Xu. Synthesis of Selenylated Spiro[indole-3,3'-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2867-2876.
[15]	Mianyuan Wu, Jun You, Yanchao Yu, Wenju Wu. A Novle Quinoline Hydrazone-Based Fluorescent Probe for Sequential Determination of Cu²⁺/Glyphosate and Its Applications [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2559-2567.

氰基硼氢化钠还原喹啉合成1,2-二氢喹啉

Synthesis of 1,2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments