Brönsted酸性离子液体催化芳香醛和2-甲基喹啉反应合成1,3-二(2-喹啉基)丙烷化合物

doi:10.7503/cjcu20150190

高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (9): 1702.doi: 10.7503/cjcu20150190

Brönsted酸性离子液体催化芳香醛和2-甲基喹啉反应合成1,3-二(2-喹啉基)丙烷化合物

刘强, 李贺, 张永红, 王斌, 孙亚栋, 阿布力米提·阿布都卡德, 刘晨江()

石油天然气精细化工教育部&自治区重点实验室, 乌鲁木齐绿色催化与合成技术重点实验室,新疆大学理化测试中心, 乌鲁木齐830046

收稿日期:2015-03-11 出版日期:2015-09-10 发布日期:2015-08-17
作者简介:联系人简介: 刘晨江, 男, 博士, 教授, 主要从事有机合成方法学和功能杂环化合物合成方面的研究. E-mail:pxylcj@126.com
基金资助:
国家自然科学基金(批准号: 21162025, 21262035)、新疆维吾尔自治区青年科技创新人才培养工程(批准号: 2014721004)和新疆大学自然科学基金(批准号: BS110133)资助

Synthesis of 1,3-Di(2-quinolyl)propane Derivatives from Aromatic Aldehyde and 2-Methyl Quinolines Catalyzed by Brönsted Acid Ionic Liquids^†

LIU Qiang, LI He, ZHANG Yonghong, WANG Bin, SUN Yadong, ABDUKADERA Ablimit, LIU Chenjiang^*()

Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Physics and Chemistry Detecting Center, Xinjiang University, Urumqi 830046, China

Received:2015-03-11 Online:2015-09-10 Published:2015-08-17
Contact: LIU Chenjiang E-mail:pxylcj@126.com
Supported by:
† Supported by the National Natural Science Foundation of China(Nos.21162025, 21262035), the Cultivation Project Young Scientific Innovative Talents of Xinjiang Uygur Autonomous Region, China(No.2014721004) and the Natural Science Foundation of Xinjiang University, China(No.BS110133)

摘要/Abstract

摘要：

以Brönsted酸性离子液体1-乙基-3-丁基咪唑对甲苯磺酸盐为催化剂, 将芳香醛和2-甲基喹啉类化合物在无溶剂或甲苯中于120 ℃反应48 h, 制备了一系列的1,3-二(2-喹啉基)丙烷化合物, 产率56%~92%, 产物结构经核磁共振波谱和高分辨质谱确证. 该方法具有简便易行、产率较高等特点.

关键词: Brönsted酸性离子液体, 1, 3-二(2-喹啉基)丙烷, 芳香醛, 2-二甲基喹啉

Abstract:

An efficient synthesis of 1,3-bis(2-quinolyl) propanes from aromatic aldehydes and 2-methyl quinolines using Brönsted acid ionic liquid 1-ethyl-3-butyl imidazol p-toluenesulfonate as catalyst was described. The reaction was heated at 120 ℃ in toluene or solvent-free for 48 h to give the desired products in yields of 56%—92%. The structures of the products were characterized by nuclear magnetic resonance spectrometry(NMR) and high-resolution mass spectrometry(HRMS). The method offers several advantages including simple work up procedure, good yields and so on.

Key words: Brönsted acid ionic liquid, 1, 3-Di(2-quinolyl)propane, Aromatic aldehyde, 2-Methyl quinoline

中图分类号:

O621.25

TrendMD:

刘强, 李贺, 张永红, 王斌, 孙亚栋, 阿布力米提·阿布都卡德, 刘晨江. Brönsted酸性离子液体催化芳香醛和2-甲基喹啉反应合成1,3-二(2-喹啉基)丙烷化合物. 高等学校化学学报, 2015, 36(9): 1702.

LIU Qiang, LI He, ZHANG Yonghong, WANG Bin, SUN Yadong, ABDUKADERA Ablimit, LIU Chenjiang. Synthesis of 1,3-Di(2-quinolyl)propane Derivatives from Aromatic Aldehyde and 2-Methyl Quinolines Catalyzed by Brönsted Acid Ionic Liquids^†. Chem. J. Chinese Universities, 2015, 36(9): 1702.

图/表 5

参考文献 23

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Compd.	Appearance	m. p./℃	ESI-MS(calcd.), m/z
3a	Orange liquid		375.1849(375.1856)[M+H]⁺
3b	Yellow liquid		389.2008(389.2012)[M+H]⁺
3c	Yellow liquid		405.1957(405.1961)[M+H]⁺
3d	Yellow liquid		409.1453(409.1463)[M+H]⁺
3e	Dark yellow liquid		409.1460(409.1463)[M+H]⁺
3f	Yellow liquid		409.1456(409.1463)[M+H]⁺
3g	Yellow liquid		420.1702(420.1707)[M+H]⁺
3h	Gray solid	159—161	420.1703(420.1707)[M+H]⁺
3i	Yellow liquid		453.0955(453.0961)[M+H]⁺
3j	Yellow liquid		393.1757(393.1762)[M+H]⁺
3k	Yellow solid	175—176	499.1155(499.1167)[M+H]⁺
3l	Dark yellow solid	164—166	499.1155(499.1167)[M+H]⁺
3m	Yellow liquid		469.1677(469.1682)[M+H]⁺
3n	Dark yellow liquid		477.0686(477.0686)[M+H]⁺
3o	Dark yellow solid	155—157	465.1563(465.1557)[M+H]⁺
3p	Gray solid	147—149	465.1562(465.1557)[M+H]⁺
3q	Yellow liquid		435.2069(435.2067)[M+H]⁺
3r	Dark yellow liquid		403.2173(403.2169)[M+H]⁺
3s	Yellow liquid		465.0898(465.0896)[M+H]⁺

Compd.	Appearance	m. p./℃	ESI-MS(calcd.), m/z
3a	Orange liquid		375.1849(375.1856)[M+H]⁺
3b	Yellow liquid		389.2008(389.2012)[M+H]⁺
3c	Yellow liquid		405.1957(405.1961)[M+H]⁺
3d	Yellow liquid		409.1453(409.1463)[M+H]⁺
3e	Dark yellow liquid		409.1460(409.1463)[M+H]⁺
3f	Yellow liquid		409.1456(409.1463)[M+H]⁺
3g	Yellow liquid		420.1702(420.1707)[M+H]⁺
3h	Gray solid	159—161	420.1703(420.1707)[M+H]⁺
3i	Yellow liquid		453.0955(453.0961)[M+H]⁺
3j	Yellow liquid		393.1757(393.1762)[M+H]⁺
3k	Yellow solid	175—176	499.1155(499.1167)[M+H]⁺
3l	Dark yellow solid	164—166	499.1155(499.1167)[M+H]⁺
3m	Yellow liquid		469.1677(469.1682)[M+H]⁺
3n	Dark yellow liquid		477.0686(477.0686)[M+H]⁺
3o	Dark yellow solid	155—157	465.1563(465.1557)[M+H]⁺
3p	Gray solid	147—149	465.1562(465.1557)[M+H]⁺
3q	Yellow liquid		435.2069(435.2067)[M+H]⁺
3r	Dark yellow liquid		403.2173(403.2169)[M+H]⁺
3s	Yellow liquid		465.0898(465.0896)[M+H]⁺

Compd.	¹H NMR(400 MHz, DMSO-d₆), δ	¹³C NMR(100 MHz, DMSO-d₆), δ
3e	8.00(d, J=8.4 Hz, 2H, NCCCH), 7.89(d, J=8.4 Hz, 2H, ArH), 7.67(m, 4H, ArH), 7.45(t, 2H, ArH), 7.26(s, 1H, ArH), 7.10(d, J=8.4 Hz, 2H, NCCH), 7.21(m, 2H, ArH), 4.06(m, 1H), 3.42(m, 4H)	160.19, 147.84, 146.00, 135.88, 133.97, 129.46, 129.27, 128.85, 126.49, 126.25, 121.99, 77.34, 77.23, 77.02, 76.70, 45.70, 45.41
3k	7.93(d, J=8.4 Hz, 2H, NCCCH), 7.86(q, 2H, ArH), 7.77(q, 2H, ArH), 7.37(m, 5H), 7.28(m, 1H, ArH), 7.15(m, 1H, ArH), 7.07(m, 1H, ArH), 4.76(m, 1H), 3.44(m, 4H)	163.23, 147.87, 140.95, 138.56, 135.51, 133.87, 131.28, 129.58, 128.52, 127.52, 127.34, 126.82, 124.14, 124.03, 122.87, 77.32, 77.00, 76.68, 43.16, 40.07
3l	8.63(d, J=2.8 Hz, 2H, ArH), 8.38(q, 2H, NCCCH), 8.07(q, 4H) 7.39(d, J=2.8 Hz, 1H, ArH), 7.30(d, J=4.0 Hz,	164.18, 149.75, 144.98, 140.18, 137.44, 134.06, 130.61, 129.66, 127.81, 127.05,
3l	2H, ArH), 7.19(m, 2H, ArH), 7.05(m, 1H, ArH), 4.70(m, 1H), 3.52(d, 4H)	125.34, 123.59, 123.59, 122.76, 77.32, 77.00, 76.68, 44.32, 76.68, 44.32
3m	7.82(d, J=8.8 Hz, 2H, NCCCH), 7.40(d, J=7.2 Hz, 1H, ArH), 7.33(t, J=7.6 Hz, 2H, ArH), 7.23(m, 3H, ArH), 7.17(d, J=8.4 Hz, 2H, NCCH), 7.10(t, J=7.2 Hz, 1H, ArH), 4.55(m, 1H), 4.07(d, J=7.6 Hz, 6H), 3.53	159.17, 155.04, 140.98, 139.63, 135.62, 134.15, 129.31, 128.66, 127.73, 127.24, 126.83, 125.63, 119.28, 107.70, 77.32, 77.00, 76.68, 56.05, 44.04
3n	7.87(d, J=8.4 Hz, 2H, NCCCH), 7.74(q, 2H, ArH), 7.54(q, 2H, ArH), 7.41(q, 1H, ArH), 7.31(m, 5H), 7.14(m, 1H, ArH), 7.07(m, 1H, ArH), 4.82(m, 1H), 3.54(m, 4H)	161.33, 143.74, 141.31, 135.92, 134.01, 133.09, 129.50, 129.13, 128.67, 127.86, 127.36, 126.76, 126.46, 125.43, 122.95, 77.32, 77.00, 76.68, 43.37, 40.86

Compd.	¹H NMR(400 MHz, DMSO-d₆), δ	¹³C NMR(100 MHz, DMSO-d₆), δ
3e	8.00(d, J=8.4 Hz, 2H, NCCCH), 7.89(d, J=8.4 Hz, 2H, ArH), 7.67(m, 4H, ArH), 7.45(t, 2H, ArH), 7.26(s, 1H, ArH), 7.10(d, J=8.4 Hz, 2H, NCCH), 7.21(m, 2H, ArH), 4.06(m, 1H), 3.42(m, 4H)	160.19, 147.84, 146.00, 135.88, 133.97, 129.46, 129.27, 128.85, 126.49, 126.25, 121.99, 77.34, 77.23, 77.02, 76.70, 45.70, 45.41
3k	7.93(d, J=8.4 Hz, 2H, NCCCH), 7.86(q, 2H, ArH), 7.77(q, 2H, ArH), 7.37(m, 5H), 7.28(m, 1H, ArH), 7.15(m, 1H, ArH), 7.07(m, 1H, ArH), 4.76(m, 1H), 3.44(m, 4H)	163.23, 147.87, 140.95, 138.56, 135.51, 133.87, 131.28, 129.58, 128.52, 127.52, 127.34, 126.82, 124.14, 124.03, 122.87, 77.32, 77.00, 76.68, 43.16, 40.07
3l	8.63(d, J=2.8 Hz, 2H, ArH), 8.38(q, 2H, NCCCH), 8.07(q, 4H) 7.39(d, J=2.8 Hz, 1H, ArH), 7.30(d, J=4.0 Hz,	164.18, 149.75, 144.98, 140.18, 137.44, 134.06, 130.61, 129.66, 127.81, 127.05,
3l	2H, ArH), 7.19(m, 2H, ArH), 7.05(m, 1H, ArH), 4.70(m, 1H), 3.52(d, 4H)	125.34, 123.59, 123.59, 122.76, 77.32, 77.00, 76.68, 44.32, 76.68, 44.32
3m	7.82(d, J=8.8 Hz, 2H, NCCCH), 7.40(d, J=7.2 Hz, 1H, ArH), 7.33(t, J=7.6 Hz, 2H, ArH), 7.23(m, 3H, ArH), 7.17(d, J=8.4 Hz, 2H, NCCH), 7.10(t, J=7.2 Hz, 1H, ArH), 4.55(m, 1H), 4.07(d, J=7.6 Hz, 6H), 3.53	159.17, 155.04, 140.98, 139.63, 135.62, 134.15, 129.31, 128.66, 127.73, 127.24, 126.83, 125.63, 119.28, 107.70, 77.32, 77.00, 76.68, 56.05, 44.04
3n	7.87(d, J=8.4 Hz, 2H, NCCCH), 7.74(q, 2H, ArH), 7.54(q, 2H, ArH), 7.41(q, 1H, ArH), 7.31(m, 5H), 7.14(m, 1H, ArH), 7.07(m, 1H, ArH), 4.82(m, 1H), 3.54(m, 4H)	161.33, 143.74, 141.31, 135.92, 134.01, 133.09, 129.50, 129.13, 128.67, 127.86, 127.36, 126.76, 126.46, 125.43, 122.95, 77.32, 77.00, 76.68, 43.37, 40.86

Compd.	R₁	R₂	Yield^b(%)	Compd.	R₁	R₂	Yield^b(%)
3a	H	H	84	3k	8-NO₂	2-Cl	92
3b	H	4-CH₃	70	3l	6-NO₂	2-Cl	76
3c	H	4-OCH₃	56	3m	8-OCH₃	2-Cl	88
3d	H	2-Cl	90	3n	8-Cl	2-Cl	75
3e	H	3-Cl	85	3o	8-NO₂	H	90
3f	H	4-Cl	64	3p	6-NO₂	H	67
3g	H	3-NO₂	86	3q	8-OCH₃	H	75
3h	H	4-NO₂	78	3r	6-CH₃	H	80
3i	H	2-Br	81	3s	8-Cl	H	67
3j	H	4-F	62

Brönsted酸性离子液体催化芳香醛和2-甲基喹啉反应合成1,3-二(2-喹啉基)丙烷化合物

Synthesis of 1,3-Di(2-quinolyl)propane Derivatives from Aromatic Aldehyde and 2-Methyl Quinolines Catalyzed by Brönsted Acid Ionic Liquids^†

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参考文献 23

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Entry	Catalyst	Molar fraction of cat.(%)	Time/h	Solvent	Temperature/℃	Yield^b(%)
1	IL1	20	24	Solvent free	120	52
2	IL2	20	24	Solvent free	120	72
3	IL3	20	24	Solvent free	120	78
4	IL3	5	24	Solvent free	120	62
5	IL3	10	24	Solvent free	120	64
6	IL3	20	24	Solvent free	80	30
7	IL3	20	24	Solvent free	100	59
8	IL3	20	24	Solvent free	140	33
9	IL3	20	12	Solvent free	120	52
10	IL3	20	48	Solvent free	120	84
11	IL3	20	48	CH₃COOC₂H₅	120	36
12	IL3	20	48	p-Xylene	120	58
13	IL3	20	48	EtOH	120	55
14	IL3	20	48	CH₃OH	120	34
15	IL3	20	48	Toluene	120	81

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Brönsted酸性离子液体催化芳香醛和2-甲基喹啉反应合成1,3-二(2-喹啉基)丙烷化合物

Synthesis of 1,3-Di(2-quinolyl)propane Derivatives from Aromatic Aldehyde and 2-Methyl Quinolines Catalyzed by Brönsted Acid Ionic Liquids†

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Synthesis of 1,3-Di(2-quinolyl)propane Derivatives from Aromatic Aldehyde and 2-Methyl Quinolines Catalyzed by Brönsted Acid Ionic Liquids^†