Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives

doi:10.6023/cjoc202301015

Abstract

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

Cite this article

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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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

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