低共熔溶剂1,3-二甲基脲/L-(+)-酒石酸中(E)-2-苯乙烯基喹啉-3-羧酸类衍生物的绿色合成

doi:10.6023/cjoc202301015

摘要/Abstract

利用环境友好且无毒无害的1,3-二甲基脲(DMU)/L-(+)-酒石酸(LTA) (n∶n=7∶3)形成的低共熔溶剂(DES)作为反应介质和催化剂使2-甲基喹啉-3-羧酸与芳醛直接进行有效的乙烯化反应, 成功实现了(E)-2-苯乙烯基喹啉-3-羧酸类衍生物的绿色合成. 所开发的合成方法具有温和且环境友好的反应条件, 实验操作简便, 后处理简单和收率高等优点, 具有很好的实际应用价值.

关键词: 绿色合成, 2-苯乙烯基喹啉, 1,3-二甲基脲, L-(+)-酒石酸, 低共熔溶剂

A green, efficient and catalyst-free synthesis of (E)-2-styrylquinoline-3-carboxylic acid derivatives via direct olefination of 2-methylquinoline-3-carboxylic acid with aromatic aldehydes has been accomplished successfully by using environmentally benign and non-toxic deep eutectic solvent (DES) of 1,3-dimethylurea (DMU)/L-(+)-tartaric acid (LTA) (n∶n=7∶3) as a dual catalyst and reaction medium. The synthetic strategy has the attractive features such as mild and environmentally benign reaction conditions, experimental simplicity, easy work-up procedure and good yields, which would contribute to the usefulness of this method.

Key words: green synthesis, 2-styrylquinoline, 1,3-dimethylurea, L-(+)-tartaric acid, deep eutectic solvent

引用此文

李阳, 袁锦鼎, 赵頔. 低共熔溶剂1,3-二甲基脲/L-(+)-酒石酸中(E)-2-苯乙烯基喹啉-3-羧酸类衍生物的绿色合成[J]. 有机化学, 2023, 43(9): 3268-3276.

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.

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参考文献 46

[1]	Dhanawat M.; Mehta D. K.; Das R. Mini-Rew. Med. Chem. 2021, 21, 1849.
[2]	Chang F. S.; Chen W.; Wang C.; Tzeng C. C.; Chen Y. L. Bioorg. Med. Chem. 2010, 18, 124.
[3]	Szczepaniak J.; Cieslik W.; Romanowicz A.; Musioł R.; Krasowska A. Int. J. Antimicrob. Agents 2017, 50, 171. doi: 10.1016/j.ijantimicag.2017.01.044
[4]	Musiol R. Curr. Pharm. Des. 2013, 19, 1835. doi: 10.2174/1381612811319100008
[5]	Kamal A.; Rahim A.; Riyaz S.; Poornachandra Y.; Balakrishna M.; Kumar C. G.; Hussaini S. M. A.; Sridhar B.; Machiraju P. K. Org. Biomol. Chem. 2015, 13, 1347. doi: 10.1039/C4OB02277G
[6]	Zwaagstra M. E.; Schoenmakers S. H.; Nederkoorn P. H.; Gelens E.; Timmerman H.; Zhang M. Q. J. Med. Chem. 1998, 41, 1439. pmid: 9554877
[7]	Luczywo A.; Sauter I. P.; Ferreira T. C. S.; Cortez M.; Romanelli G. P.; Sathicq G.; Asís S. E. J. Heterocycl. Chem. 2021, 58, 822. doi: 10.1002/jhet.v58.3
[8]	Mittal R. K.; Purohit P. Anti-Cancer Agents Med. Chem. 2021, 21, 1708. doi: 10.2174/1871520620999201124214112
[9]	Latha D. S.; Yaragorla S. Eur. J. Org. Chem. 2020, 2020, 2155. doi: 10.1002/ejoc.v2020.15
[10]	Fakhfakh M. A.; Franck X.; Fournet A.; Hocquemiller R.; Figadere B. Synth. Commun. 2002, 32, 2863. doi: 10.1081/SCC-120006472
[11]	Xia H.; Liu Y.; Zhao P.; Gou S.; Wang J. Org. Lett. 2016, 18, 1796. doi: 10.1021/acs.orglett.6b00522
[12]	Rubtsov M. V.; Pershin G. N.; Yanbuktin N. A.; Pelenitsina L. A.; Gurevich T. J.; Novitskaya N. A.; Milovanova S. N.; Vichkanova S. A. J. Med. Chem. 1959, 2, 113. doi: 10.1021/jm50009a001
[13]	Mao D.; Hong G.; Wu S.; Liu X.; Yu J.; Wang L. Eur. J. Org. Chem. 2014, 2014, 3009. doi: 10.1002/ejoc.201400073
[14]	Dang H. T.; Lieu T. N.; Truong T.; Phan N. T. J. Mol. Catal. A: Chem. 2016, 420, 237. doi: 10.1016/j.molcata.2016.04.022
[15]	Pi D.; Jiang K.; Zhou H.; Sui Y.; Uozumi Y.; Zou K. RSC Adv. 2014, 4, 57875. doi: 10.1039/C4RA10939B
[16]	Jamal Z.; Teo Y. C.; Lim G. S. Tetrahedron 2016, 72, 2132. doi: 10.1016/j.tet.2016.03.004
[17]	Jamal Z.; Teo Y. C. Synlett 2014, 25, 2049. doi: 10.1055/s-00000083
[18]	Yaragorla S.; Singh G.; Dada R. Tetrahedron Lett. 2015, 56, 5924. doi: 10.1016/j.tetlet.2015.09.035
[19]	Li V. M.; Gavrishova T. N.; Budyka M. F. Russ. J. Org. Chem. 2012, 48, 823. doi: 10.1134/S1070428012060139
[20]	Musiol R.; Podeszwa B.; Finster J.; Niedbala H.; Polanski J. Monatsh. Chem. 2006, 137, 1211. doi: 10.1007/s00706-006-0513-1
[21]	Xu L.; Shao Z.; Wang L.; Zhao H.; Xiao J. Tetrahedron Lett. 2014, 55, 6856. doi: 10.1016/j.tetlet.2014.10.079
[22]	Liang E.; Wang J.; Wu Y.; Huang L.; Yao X.; Tang X. Adv. Synth. Catal. 2019, 361, 3619. doi: 10.1002/adsc.201900351
[23]	Dabiri M.; Salehi P.; Baghbanzadeh M.; Nikcheh M. S. Tetrahedron Lett. 2008, 49, 5366. doi: 10.1016/j.tetlet.2008.06.054
[24]	Sarma P.; Saikia S.; Borah R. Synth. Commun. 2016, 46, 1187. doi: 10.1080/00397911.2016.1193754
[25]	Han Y.; Zhang M.; Zhang Y. Q.; Zhang Z. H. Green Chem. 2018, 20, 4891. doi: 10.1039/C8GC02611D
[26]	Fu S.; Wang L.; Dong H.; Yu J.; Xu L.; Xiao J. Tetrahedron Lett. 2016, 57, 4533. doi: 10.1016/j.tetlet.2016.08.065
[27]	Smith E. L.; Abbott A. P.; Ryder K. S. Chem. Rev. 2014, 114, 11060. doi: 10.1021/cr300162p pmid: 25300631
[28]	Alonso D. A.; Baeza A.; Chinchilla R.; Guillena G.; Pastor I. M.; Ramòn D. J. Eur. J. Org. Chem. 2016, 2016, 612. doi: 10.1002/ejoc.201501197
[29]	Zheng L. L.; Wang Y. Q.; Li X. G.; Zhang W. B. Chin. J. Org. Chem. 2022, 42, 3714. (in Chinese) doi: 10.6023/cjoc202206002
	(郑露露, 王雨晴, 李小港, 张文彬, 有机化学, 2022, 42, 3714.) doi: 10.6023/cjoc202206002
[30]	Xiao L. W.; Liu G. X.; Li Z.; Ren P.; Ren L. L.; Kong J. Chin. J. Org. Chem. 2020, 40, 2988. (in Chinese)
	(肖立伟, 刘光仙, 李政, 任萍, 任丽磊, 孔洁, 有机化学, 2020, 40, 2988.) doi: 10.6023/cjoc202003043
[31]	Zhang M.; Liu Y. H.; Shang Z. R.; Hu H. C.; Zhang Z. H. Catal. Commun. 2017, 88, 39. doi: 10.1016/j.catcom.2016.09.028
[32]	Zhang W. H.; Chen M. N.; Hao Y.; Jiang X.; Zhou X. L.; Zhang Z. H. J. Mol. Liq. 2019, 278, 124. doi: 10.1016/j.molliq.2019.01.065
[33]	Xu L.; Zhang W. H.; Cui Z. S.; Zhang Z. H. Curr. Organocatal. 2021, 8, 249.
[34]	Upadhyay A.; Kushwaha P.; Gupta S.; Dodda R. P.; Ramalingam K.; Kant R.; Goyal N. Eur. J. Med. Chem. 2018, 154, 172. doi: 10.1016/j.ejmech.2018.05.014
[35]	Pawar P. M.; Jarag K. J.; Shankarling G. S. Green Chem. 2011, 13, 2130. doi: 10.1039/c0gc00712a
[36]	Srivastava S. ChemistrySelect 2020, 5, 799. doi: 10.1002/slct.v5.2
[37]	Sanap A. K.; Shankarling G. S. RSC Adv. 2014, 4, 34938. doi: 10.1039/C4RA05858E
[38]	Hu H. C.; Liu Y. H.; Li B. L.; Cui Z. S.; Zhang Z. H. RSC Adv. 2015, 5, 7720. doi: 10.1039/C4RA13577F
[39]	Abbott A. P.; Boothby D.; Capper G.; Davies D. L.; Rasheed R. K. J. Am. Chem. Soc. 2004, 126, 9142. doi: 10.1021/ja048266j
[40]	Bafti B.; Khabazzadeh H. J. Chem. Sci. 2014, 126, 881. doi: 10.1007/s12039-014-0624-x
[41]	Wang P.; Ma F. P.; Zhang Z. H. J. Mol. Liq. 2014, 198, 259. doi: 10.1016/j.molliq.2014.07.015
[42]	Ali R.; Chinnam A. K.; Aswar V. R. Curr. Org. Chem. 2021, 25, 554. doi: 10.2174/1385272825666210111111313
[43]	Gore S.; Baskaran S.; König B. Org. Lett. 2012, 14, 4568. doi: 10.1021/ol302034r
[44]	Krishnakumar V.; Vindhya N. G.; Mandal B. K.; Nawaz Khan F. R. Ind. Eng. Chem. Res. 2014, 53, 10814. doi: 10.1021/ie501320a
[45]	Alvi S.; Ali R. Org. Biomol. Chem. 2021, 19, 9732. doi: 10.1039/D1OB01618K
[46]	Kaminsky D.; Meltzer R. I. J. Med. Chem. 1968, 11, 160. pmid: 5637164

Entry	Compd.	Ar	Yield^b/%	m.p./℃
1	3a	C₆H₅	84	218~220
2	3b	4-MeC₆H₄	81	198~199
3	3c	3-MeOC₆H₄	80	184~185
4	3d	2,3-(MeO)₂C₆H₃	62	192~194
5	3e	2,4-(MeO)₂C₆H₃	66	221~222
6	3f	2,4,5-(MeO)₃C₆H₂	63	239~241
7	3g	3,4,5-(MeO)₃C₆H₂	76	211~213
8	3h	4-ClC₆H₄	85	257~258
9	3i	3,5-Cl₂C₆H₃	84	198~200
10	3j	3-BrC₆H₄	79	190~192
11	3k	4-BrC₆H₄	87	238~240
12	3l	4-CNC₆H₄	78	261~263
13	3m		82	175~178
14	3n		76	197~198
15	3o		81	181~182
16	3p		84	195~196

Entry	Compd.	Ar	Yield^b/%	m.p./℃
1	3a	C₆H₅	84	218~220
2	3b	4-MeC₆H₄	81	198~199
3	3c	3-MeOC₆H₄	80	184~185
4	3d	2,3-(MeO)₂C₆H₃	62	192~194
5	3e	2,4-(MeO)₂C₆H₃	66	221~222
6	3f	2,4,5-(MeO)₃C₆H₂	63	239~241
7	3g	3,4,5-(MeO)₃C₆H₂	76	211~213
8	3h	4-ClC₆H₄	85	257~258
9	3i	3,5-Cl₂C₆H₃	84	198~200
10	3j	3-BrC₆H₄	79	190~192
11	3k	4-BrC₆H₄	87	238~240
12	3l	4-CNC₆H₄	78	261~263
13	3m		82	175~178
14	3n		76	197~198
15	3o		81	181~182
16	3p		84	195~196