Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives

doi:10.6023/cjoc202101024

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2788-2799.DOI: 10.6023/cjoc202101024 Previous Articles Next Articles

ARTICLES

4-羟基香豆素在四氢喹啉及二香豆素内盐合成中的应用

杨晓宇^a, 柳建林^a, 胡方芝^a, 孙红梅^a, 王亮^a^,^b^,^*(), 李帅帅^a^,^b^,^*()

a 青岛农业大学化学与药学院山东青岛 266109
b 青岛科技大学化学与分子工程学院山东青岛 266042

收稿日期:2021-01-16 修回日期:2021-03-23 发布日期:2021-04-12
通讯作者: 王亮, 李帅帅
作者简介:
† 共同第一作者(These authors contributed equally to this work).
基金资助:
国家自然科学基金(21978144); 国家自然科学基金(21702117); 国家自然科学基金(21776148); 山东省重点研发计划(2018GSF118224); 山东省重点研发计划(2019GSF108020); 山东省重点研发计划(2019RKB01027); 山东省青创科技计划(2019KJM002); 青岛科技大学开放基金(QUSTHX201916); 青岛科技大学开放基金(QUSTHX202004)

Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives

Xiaoyu Yang^a, Jianlin Liu^a, Fangzhi Hu^a, Hongmei Sun^a, Liang Wang^a^,^b(), Shuai-Shuai Li^a^,^b()

a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
b College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042

Received:2021-01-16 Revised:2021-03-23 Published:2021-04-12
Contact: Liang Wang, Shuai-Shuai Li
Supported by:
National Natural Science Foundation of China(21978144); National Natural Science Foundation of China(21702117); National Natural Science Foundation of China(21776148); Key Research & Development Program of Shandong Province(2018GSF118224); Key Research & Development Program of Shandong Province(2019GSF108020); Key Research & Development Program of Shandong Province(2019RKB01027); Support Plan on Science and Technology for Youth Innovation of Universities in Shandong Province(2019KJM002); Opening Funding of Qingdao University of Science & Technology(QUSTHX201916); Opening Funding of Qingdao University of Science & Technology(QUSTHX202004)

1. .pdf(2555KB)

Abstract

The pharmaceutically significant 3-mono-substituted tetrahydroquinoline derivatives carryingortho-hydroxy- benzoyl moiety are constructed via EtOH mediated cascade Knoevenagel condensation/[1,5]-hydride transfer/cyclization/hydrolysis/decarboxylation from 4-hydroxycoumarins ando-aminobenzaldehydes. In addition, the substrate-controlled diverse syntheses also could be achieved, and a variety of the zwitterionic biscoumarin derivatives are facilely provided under catalyst- and solvent-free conditions at room temperature.

Key words: 4-hydroxycoumarin, hydride-transfer reaction, tetrahydroquinoline, zwitterionic biscoumarin

Cite this article

Xiaoyu Yang, Jianlin Liu, Fangzhi Hu, Hongmei Sun, Liang Wang, Shuai-Shuai Li. Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2788-2799.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

Figure 1. Representative bioactive molecules containing tetrahydroquinoline or biscoumarin skeleton

Scheme 1. Construction of tetrahydroquinoline skeletons via hydride transfer strategy

Entry^a	Catalyst	Solvent	Yield^b/%
Entry^a	Catalyst	Solvent	3a	4a
1	Pyrrolidine	EtOH	30	40
2	Piperidine	EtOH	38	38
3	Morpholine	EtOH	33	42
4	Et₃N	EtOH	29	36
5	Na₂CO₃	EtOH	36	26
6	Morpholine	MeOH	35	38
7	Morpholine	CH₃CN	89	Trace
8	Morpholine	DCE	93	Trace
9	—	EtOH	55	Trace
10^c	Morpholine	EtOH	35	40
11^d	Morpholine	EtOH	18	30
12^e	Morpholine	EtOH	20	59
13^f	Morpholine	EtOH	Trace	80
14^f	Morpholine	H₂O	Trace	76

Table 1. Optimization of the reaction conditionsa

Table 2. Scope of o-aminobenzaldehydes for synthesis of 3-benzoyl tetrahydroquinolinesa

Table 3. Substrate scope for the synthesis of 3-benzoyl tetrahydroquinolinesa

Scheme 2. Confirmation of the relative configuration of the main diastereoisomer

Table 4. The scope for synthesis of zwitterionic biscoumarin derivativesa

Scheme 3. A plausible mechanism

References 11

[1]	(a) Takemura, T.; Kamo, T.; Sakuno, E.; Hiradate, S.; Fujii, Y. J. Trop. For. Sci. 2013, 25,268.
	(b) Mangasuli,S. N.; Hosamani,K. M.; Devarajegowda,H. C.; Kurjogi,M. M.; Joshi,S. D. Eur. J. Med. Chem. 2018, 146,747. doi: 10.1016/j.ejmech.2018.01.025
	(c) Keri,R. S.; Sasidhar,B. S.; Nagaraja,B. M.; Santos,M. A. Eur. J. Med. Chem. 2015, 100,257. doi: 10.1016/j.ejmech.2015.06.017
	(d) Amin,K. M.; Eissa,A. A.M.; Abou-Seri,S. M.; Awadallah,F. M.; Hassan,G. S. Eur. J. Med. Chem. 2013, 60,187. doi: 10.1016/j.ejmech.2012.12.004
	(e) Paul, K.; Bindal, S.; Luxami, V. Bioorg. Med. Chem. Lett. 2013, 23,3667.
	(f) Shi, L.; Li, Z.; Cui, X.; Zhu, T.; Pang, X.; Li, L.; Luo, D.; Liu, F.; Zhao, B.; Long, Y.; Zhang, S. Chin. J. Org. Chem. 2020, 40,1598 (in Chinese). doi: 10.6023/cjoc201911028
	( 时蕾, 李子秋, 崔鑫鑫, 朱挺, 庞晓静, 李龙辉, 罗德福, 刘方芳, 赵冰玉, 龙跃, 张赛扬, 有机化学, 2020, 40,1598.)
[2]	For selected recent examples on 4-hydroxycoumarin as synthon, see: (a) Miao, M.; Luo, Y.; Li, H.; Xu, X.; Chen, Z.; Xu, J.; Ren,, H. J. Org. Chem. 2016, 81,5228. doi: 10.1021/acs.joc.6b00734
	(b) Chen, Y.; Wang, Y.; Zhong, R.; Li, J. J. Org. Chem. 2020, 85,10638. doi: 10.1021/acs.joc.0c01207
	(c) Mukherjee, S.; Pramanik, A. ACS Sustainable Chem. Eng. 2020, 8,403. doi: 10.1021/acssuschemeng.9b05682
	(d) Xu, R.; Li, K.; Wang, J.; Lu, J.; Pan, L.; Zeng, X.; Zhong, G. Chem. Commun. 2020, 56,8404. doi: 10.1039/D0CC02832K
	(e) Sharma, K.; Neog, K.; Gogoi, P. Org. Lett. 2020, 22,73. doi: 10.1021/acs.orglett.9b03932
	(f) Zhu, F.; Wang, Y.; He, M.; Yan, Z.; Lin, S. Chin. J. Org. Chem. 2019, 39,1175 (in Chinese).
	( 朱福元, 王彦梅, 何明闯, 严兆华, 林森, 有机化学, 2019, 39,1175.)
	(g) Rezaei, R.; Moezzi, F.; Doroodmand,M. M. Chin. Chem. Lett. 2014, 25,183. doi: 10.1016/j.cclet.2013.10.033
	(h) Chen, Z.; Bi, J.; Su, W. Chin. J. Chem. 2013, 31,507. doi: 10.1002/cjoc.201201130
	(i) Hamid Reza, S.; Moones, H. Chin. J. Chem. 2009, 27,1795. doi: 10.1002/cjoc.v27:9
[3]	(a) Spadoni, G.; Bedini, A.; Lucarini, S.; Mari, M.; Caignard,D. -H.; Boutin,J. A.; Delagrange, P.; Lucini, V.; Scaglione, F.; Lodola, A.; Zanardi, F.; Pala, D.; Mor, M.; Rivara, S. J. Med. Chem. 2015, 58,7512. doi: 10.1021/acs.jmedchem.5b01066
	(b) Ruble,J. C.; Hurd,A. R.; Johnson,T. A.; Sherry,D. A.; Barbachyn,M. R.; Toogood,P. L.; Bundy,G. L.; Graber,D. R.; Kamilar,G. M. J. Am. Chem. Soc. 2009, 131,3991. doi: 10.1021/ja808014h
	(c) Taylor,S. N.; Marrazzo, J.; Batteiger,B. E.; Hook,E. W.; Seña,A. C.; Long, J.; Wierzbicki,M. R.; Kwak, H.; Johnson,S. M.; Lawrence, K.; Mueller, J. N. Engl. J. Med. 2018, 379,1835. doi: 10.1056/NEJMoa1706988
	(d) Yu, L.; Ding, Q.; Song, C.; Chang, J. Chin. J. Org. Chem. 2021, 41,2507 (in Chinese). doi: 10.6023/cjoc202101025
	( 余璐璐, 丁群山, 宋传君, 常俊标, 有机化学, 2021, 41,2507.)
[4]	For reviews on tetrahydroquinolines, see: (a) Sridharan, V.; Suryavanshi, P.; Menendez,,J. C. Chem. Rev. 2011, 111,7157. doi: 10.1021/cr100307m
	(b) Muthukrishnan, I.; Sridharan, V.; Menendez,J. C. Chem. Rev. 2019, 119,5057. doi: 10.1021/acs.chemrev.8b00567
	For representative examples on tetrahydroquinolines, see: (c) Jadhav,A. M.; Pagar,V. V.; Liu,R. -S. Angew. Chem.,Int. Ed. 2012, 51,11809. doi: 10.1002/anie.201205692
	(d) Zhang, X.; Han, X.; Lu, X. Org. Lett. 2015, 17,3910. doi: 10.1021/acs.orglett.5b01894
	(e) Leth,L. A.; Glaus, F.; Meazza, M.; Fu, L.; Thøgersen,M. K.; Bitsch,E. A.; Jørgensen,K. A. Angew. Chem.,Int. Ed. 2016, 55,15272. doi: 10.1002/anie.v55.49
	(f) Bianchini, G.; Ribelles, P.; Becerra, D.; Ramos,M. T.; Menendez,J. C. Org. Chem. Front. 2016, 3,412. doi: 10.1039/C6QO00037A
	(g) Xu,G. -Q.; Li,C. -G.; Liu,M. -Q.; Cao, J.; Luo,Y. -C.; Xu,P. -F. Chem. Commun. 2016, 52,1190. doi: 10.1039/C5CC08833J
	(h) Zhang, Z.; Song, X.; Li, G.; Li, X.; Zheng, D.; Zhao, X.; Miao, H.; Zhang, G.; Liu, L. Chin. Chem. Lett. 2021, 32,1423. doi: 10.1016/j.cclet.2020.11.001
	(i) Qian,L. F.; Zhou,Y. H.; Zhang, W. Chin. Chem. Lett. 2009, 20,805. doi: 10.1016/j.cclet.2009.03.006
	(j) Zhang, Z.; Zhang, Q.; Yan, Z.; Liu, Q. J. Org. Chem. 2007, 72,9808. doi: 10.1021/jo701551f
[5]	For reviews on hydride transfer reactions, see: (a) Tobisu, M.; Chatani,, N. Angew. Chem.,Int. Ed. 2006, 45,1683. doi: 10.1002/(ISSN)1521-3773
	(b) Peng, B.; Maulide, N. Chem.-Eur. J. 2013, 19,13274. doi: 10.1002/chem.201301522
	(c) Wang, L.; Xiao, J. Adv. Synth. Catal. 2014, 356,1137. doi: 10.1002/adsc.v356.6
	(d) Pan,S. C. Beilstein J. Org. Chem. 2012, 8,1374. doi: 10.3762/bjoc.8.159
	(e) Haibach,M. C.; Seidel, D. Angew. Chem.,Int. Ed. 2014, 53,5010.
	(f) Kwon,S. J.; Kim,D. Y. Chem. Rec. 2016, 16,1191. doi: 10.1002/tcr.201600003
	(g) Xiao, M.; Zhu, S.; Shen, Y.; Wang, L.; Xiao, J. Chin. J. Org. Chem. 2018, 38,328 (in Chinese). doi: 10.6023/cjoc201708024
	肖明艳, 朱帅, 沈耀滨, 王亮, 肖建, 有机化学, 2018, 38,328.).
	Other representative works on redox-neutral reactions, see:.
	(g) Yang, L.; Wei, L.; Wan,J. -P. Chem. Commun. 2018, 54,7475. doi: 10.1039/C8CC03514H
	(h) Yang, L.; Wan,J. -P. Green Chem. 2020, 22,3074. doi: 10.1039/D0GC00738B
	(i) Huang, H.; Deng, K.; Deng,G. -J. Green Chem. 2020, 22,8243. doi: 10.1039/D0GC02789H
	(j) Xiao, K.; Huang, Y.; Huang, P. Acta Chim. Sinica 2012, 70,1917. doi: 10.6023/A12080542
	(k) G. H; Huang,P. -Q. Chin. J. Chem. 2019, 37,811. doi: 10.1002/cjoc.v37.8
[6]	For selected examples on electron-withdrawing groups substituted alkenes as hydride acceptors, see: (a) Mahoney,S. J.; Moon,D. T.; Hollinger, J.; Fillion,, E. Tetrahedron Lett. 2009, 50,4706. doi: 10.1016/j.tetlet.2009.06.007
	(b) Mori, K.; Kawasaki, T.; Sueoka, S.; Akiyama, T. Org. Lett. 2010, 12,1732. doi: 10.1021/ol100316k
	(c) Mori, K.; Sueoka, S.; Akiyama, T. J. Am. Chem. Soc. 2011, 133,2424. doi: 10.1021/ja110520p
	(d) Jeong,H. I.; Youn,T. H.; Kim,D. Y. Bull. Korean Chem. Soc. 2017, 38,421. doi: 10.1002/bkcs.2017.38.issue-4
	(e) Briones,J. F.; Basarab,G. S. Chem. Commun. 2016, 52,8541. doi: 10.1039/C6CC03600G
	(f) Yoshida, T.; Mori, K. Chem. Commun. 2017, 53,4319. doi: 10.1039/C7CC01717K
	(g) Yamazaki, S.; Naito, T.; Tatsumi, T.; Kakiuchi, K. ChemistrySelect 2018, 3,4505. doi: 10.1002/slct.201800447
[7]	Representative one-pot reactions for construction of tetrahydroquinoline skeletons, see: (a) Wang,P. -F.; Jiang,C. -H.; Wen, X.; Xu,Q. -L.; Sun,, H. J. Org. Chem. 2015, 80,1155. doi: 10.1021/jo5026817
	(b) Bai, G.; Dong, F.; Xu, L.; Liu, Y.; Wang, L.; Li,S. -S. Org. Lett. 2019, 21,6225. doi: 10.1021/acs.orglett.9b02051
	(c) Chen, C.; Xu, L.; Wang, L.; Li,S. -S. Org. Biomol. Chem. 2018, 16,7109. doi: 10.1039/C8OB02012D
	(d) Li,S. -S.; Lv, X.; Ren, D.; Shao,C. -L.; Liu, Q.; Xiao, J. Chem. Sci. 2018, 9,8253. doi: 10.1039/C8SC03339K
	(e) Yang, X.; Hu, F.; Wang, L.; Xu, L.; Li,S. -S. Org. Biomol. Chem. 2020, 18,4267. doi: 10.1039/D0OB00521E
	(f) Shen,Y. -B.; Wang,L. -X.; Sun,Y. -M.; Dong,F. -Y.; Yu, L.; Liu, Q.; Xiao, J. J. Org. Chem. 2020, 85,1915. doi: 10.1021/acs.joc.9b02606
	(g) Zhu, S.; Chen, C.; Xiao, M.; Yu, L.; Wang, L.; Xiao, J. Green Chem. 2017, 19,5653. doi: 10.1039/C7GC02353G
	(h) Liu, S.; Wang, H.; Wang, B. Org. Biomol. Chem. 2020, 18,8839. doi: 10.1039/D0OB01887B
[8]	(a) Li,S. -S.; Zhu, S.; Chen, C.; Duan, K.; Liu, Q.; Xiao, J. Org. Lett. 2019, 21,1058. doi: 10.1021/acs.orglett.8b04100
	(b) Li,S. -S.; Zhou, L.; Wang, L.; Zhao, H.; Yu, L.; Xiao, J. Org. Lett. 2018, 20,138. doi: 10.1021/acs.orglett.7b03492
	(c) Zhu, S.; Chen, C.; Duan, K.; Sun,Y. -M.; Li,S. -S.; Liu, Q.; Xiao, J. J. Org. Chem. 2019, 84,8440. doi: 10.1021/acs.joc.9b00489
	(d) Lü, X.; Hu, F.; Duan, K.; Li,S. -S.; Liu, Q.; Xiao, J. J. Org. Chem. 2019, 84,1833. doi: 10.1021/acs.joc.8b02754
	(e) Shi, H.; Xu, L.; Ren, D.; Wang, L.; Guo, W.; Li,S. -S. Org. Biomol. Chem. 2020, 18,4267. doi: 10.1039/D0OB00521E
	(f) Duan, K.; Shi, H.; Wang,L. -X.; Li,S. -S.; Xu L.; Xiao, J. Org. Chem. Front. 2020, 7,2511. doi: 10.1039/D0QO00658K
	(g) Yuan, K.; Dong, F.; Yin, X.; Li,S. -S.; Wang, L.; Xu, L. Org. Chem. Front. 2020, 7,3868. doi: 10.1039/D0QO00972E
	(h) Xing, Y.; Dong, F.; Yin, X.; Wang, L.; Li,S. -S. Asian J. Org. Chem. 2020, 9,1787. doi: 10.1002/ajoc.v9.11
	(i) Yang, X.; Wang, L.; Hu, F.; Xu, L.; Li, S.; Li,S. -S. Org. Lett. 2021, 23,358. doi: 10.1021/acs.orglett.0c03863
	(j) Guo, M.; Dong, F.; Yin, X.; Wang, L.; Li,S. -S. Org. Chem. Front. 2021, 8,2224. doi: 10.1039/D0QO01622E
[9]	(a) Chauncey,M. A.; Grundon,M. F.; Rutherford,M. J. J. Chem. Soc.,Chem. Commun. 1988, 0,527.
	(b) Zhang, K.; Han, H.; Wang, L.; Zhang, Z.; Wang, Q.; Zhang, W.; Bu, Z. Chem. Commun. 2019, 55,13681. doi: 10.1039/C9CC07114H
[10]	(a) Musa,M. A.; Cooperwood,J. S.; Khan,M. O.F. Curr. Med. Chem. 2008, 15,2664. doi: 10.2174/092986708786242877
	(b) Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke,S. L.; Lee,K. H. Med. Res. Rev. 2003, 23,322. doi: 10.1002/(ISSN)1098-1128
	(c) Anand, P.; Singh, B.; Singh, N. Bioorg. Med. Chem. 2012, 20,1175. doi: 10.1016/j.bmc.2011.12.042
	(d) Saeed, A.; Haroon, M.; Muhammad, F.; Larik,F. A.; Hesham,E. S.; Channar,P. A. J. Organomet. Chem. 2017, 834,88. doi: 10.1016/j.jorganchem.2017.02.016
	(e) Khan,K. M.; Iqbal, S.; Lodhi,M. A.; Maharvi,G. M.; Ullah, Z.; Choudhary,M. I.; Rahman, A.; Perveen, S. Bioorg. Med. Chem. 2004, 12,1963.
[11]	(a) Bavandia, H.; Habibia, Z.; Yousefi, M. Bioorg. Chem. 2020, 103,104139. doi: 10.1016/j.bioorg.2020.104139
	(b) Zeynizadeh, B.; Gilanizadeh, M. New J. Chem. 2019, 43,18794. doi: 10.1039/C9NJ04718B
	(c) Mathavan, S.; Kannan, K.; Yamajala,R. B.R.D. Org. Biomol. Chem. 2019, 17,9620. doi: 10.1039/C9OB02090J
	(d) Yang, C.; Su,W. -Q.; Xu,D. -Z. RSC Adv. 2016, 6,99656. doi: 10.1039/C6RA23018K

[1]	Lulu Yu, Qunshan Ding, Chuanjun Song, Junbiao Chang. Enantioselective Total Synthesis of (–)-Angustureine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2507-2510.
[2]	Zhaohui Xu, Huatao Ye, Wenfeng Zhang, Qiang Xiao. A Four-Component Reaction for the Synthesis of Dispirotetrahydro-quinoline-bis(1,3-dioxane-4,6-dione) Derivatives Catalyzed by Tartaric Acid [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2127-2133.
[3]	Sun Wanwan, Mao Yujian, Jiang Jing, Yu Jing, Chen Lingyun, Hu Yanwei, Zhang Shilei. Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil [J]. Chin. J. Org. Chem., 2019, 39(9): 2525-2533.
[4]	Chen Xiaoling, Chen Jingwen, Bao Zongbi, Yang Qiwei, Yang Yiwen, Ren Qilong, Zhang Zhiguo. MIL-101(Cr)-SO₃H Catalyzed Transfer Hydrogenation of 2-Substituted Quinoline Derivatives [J]. Chin. J. Org. Chem., 2019, 39(6): 1681-1687.
[5]	Zhu Fuyuan, Wang Yanmei, He Mingchuang, Yan Zhaohua, Lin Sen. Tetrabutylammonium Iodide Promoted Thioetherification of Arylsulfonylhydrazides with 4-Hydroxycoumarins [J]. Chin. J. Org. Chem., 2019, 39(4): 1175-1180.
[6]	Zhang Xiaoming, Lei Peng, Li Xinlu, Yang Xinling, Zhang Xuebo, Sun Tengda, Ling Yun. Synthesis and Anti-fungual Activity of Novel Aspernigerin Derivatives Containing Thiocarbonyl Moiety [J]. Chin. J. Org. Chem., 2018, 38(12): 3197-3203.
[7]	Wang Daolin, Yang Feifei, Liu Zhong, Dong Zhe, Zhao Wei. Synthesis of Coumarino[4,3-b]pyran-4-one Derivatives [J]. Chin. J. Org. Chem., 2014, 34(1): 204-209.
[8]	Wu Qinglai, Li Yongqiang, Yang Xinling, Ling Yun. Synthesis and Bioactivity of Aspernigerin Analogues [J]. Chin. J. Org. Chem., 2012, 32(04): 747-754.
[9]	ZHANG Sheng-Ling, HUANG Zhi-Shu, GU Lian-Quan. Synthesis of Benzoxazolo[3,2-a]pyridinium Zwitterions [J]. Chin. J. Org. Chem., 2010, 30(06): 933-936.
[10]	ZHOU Jian-Feng, GONG Gui-Xia, AN Li-Chao, SUN Xiao-Jun, SHU Feng-Xia. Synthesis of 3,3-Arylidene bis(4-hydroxycoumarin) Catalyzed by Sulfamic Acid in Aqueous Media under Microwave Irradiation [J]. Chin. J. Org. Chem., 2009, 29(12): 1988-1991.
[11]	GAO, Wen-Tao*; HOU, Wen-Duan; ZHENG, Mei-Ru. Facile Preparation and Fluorescent Properties of 4-Hydroxycoumarin and Its Derivatives [J]. Chin. J. Org. Chem., 2008, 28(11): 2011-2015.
[12]	WANG Xiang-Shan*^,1,2,3,ZENG Zhao-Sen^1,3,SHI Da-Qing^1,3 WEI Xian-Yong²,ZONG Zhi-Min². One-pot Synthesis of 2-Amino-4-aryl-4H-pyrano[3,2-c]coumarinDe-rivatives Using KF/Al₂O₃ as Catalyst [J]. Chin. J. Org. Chem., 2005, 25(9): 1138-1141.
[13]	WANG Jing,SHI Da-Qing*,ZHUANG Qi-Ya,WANG Xiang-Shan TU Shu-Jiang. Clean Synthesis of α,α-Bis(4-hydroxycoumarin-3-yl)toluene in Aque-ous Media [J]. Chin. J. Org. Chem., 2005, 25(08): 926-929.

4-羟基香豆素在四氢喹啉及二香豆素内盐合成中的应用

Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 11

Related Articles 13

Recommended Articles

Metrics

Comments