One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives

doi:10.6023/cjoc201903032

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3299-3303.DOI: 10.6023/cjoc201903032 Previous Articles Next Articles

三组分一锅法合成3-苯并[d]咪唑色烯衍生物

王翔*(), 陈平, 支三军, 胡华友, 阚玉和, 张载超*()

淮阴师范学院化学化工学院江苏省低维材料化学重点实验室江苏淮安 223300

收稿日期:2019-03-17 发布日期:2019-06-19
通讯作者: 王翔,张载超 E-mail:hurricanwx@163.com;zhangzc@hytc.edu.cn
基金资助:
国家自然科学基金(21601061);国家自然科学基金(51403073);江苏省高校面上基金(16KJB150006);江苏省低维材料化学重点实验室开放基金(JSKC15145)

One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives

Wang Xiang*(), Chen Ping, Zhi Sanjun, Hu Huayou, Kan Yuhe, Zhang Zaichao*()

Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an, Jiangsu 223300

Received:2019-03-17 Published:2019-06-19
Contact: Wang Xiang,Zhang Zaichao E-mail:hurricanwx@163.com;zhangzc@hytc.edu.cn
Supported by:
the National Natural Science Foundation of China(21601061);the National Natural Science Foundation of China(51403073);the Department of Education of Jiangsu Province(16KJB150006);the Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials(JSKC15145)

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Abstract

Benzoimidazole and chromen derivatives exhibit a variety of important biological activities. Chromens incorporating benzoimidazole moiety have high Rho kinase inhibitory activity. However, the effective synthetic method for the preparation of these compounds is rare. The efficient synthesis of new substituted 3-(1H-benzo[d]imidazol-2-yl)-4H-chromens in 48%~89% yields via one-pot, three-component reaction of 2-(1H-benzo[d]imidazol-2-yl)acetonitrile with aromatic aldehydes and 5, 5-dimethylcyclohexane-1, 3-dione was studied. This reaction was carried out in EtOH in the presence of pyridine under reflux conditions. All reactions were completed within 1 to 3 h.

Key words: benzoimidazole, chromen, multicomponent reaction, heterocyclic skeleton

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Wang Xiang, Chen Ping, Zhi Sanjun, Hu Huayou, Kan Yuhe, Zhang Zaichao. One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3299-3303.

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Fig. & Tab. 4

References 6

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Entry	Catalyst	Yield^b/%
1	CBr₄	31
2	Et₃N	79
3	Piperidine	29
4	Morpholine	65
5	Pyridine	85


Entry	Catalyst	Yield^b/%
1	CBr₄	31
2	Et₃N	79
3	Piperidine	29
4	Morpholine	65
5	Pyridine	85


Entry	4	Ar	Time/h	Yield^b/%
1	4a	4-Bromophenyl	2	85
2	3b	4-Chlorophenyl	2	79
3	4c	4-Fluorophenyl	2	72
4	4d	4-Methoxyphenyl	3	56
5	4e	3-Nitrophenyl	1	89
6	4f	2-Cyanophenyl	2	48
7	4g	2, 3-Dichlorophenyl	2	79
8	4h	2, 4-Dichlorophenyl	2	75
9	4i	3, 4-Dichlorophenyl	2	63


Entry	4	Ar	Time/h	Yield^b/%
1	4a	4-Bromophenyl	2	85
2	3b	4-Chlorophenyl	2	79
3	4c	4-Fluorophenyl	2	72
4	4d	4-Methoxyphenyl	3	56
5	4e	3-Nitrophenyl	1	89
6	4f	2-Cyanophenyl	2	48
7	4g	2, 3-Dichlorophenyl	2	79
8	4h	2, 4-Dichlorophenyl	2	75
9	4i	3, 4-Dichlorophenyl	2	63

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三组分一锅法合成3-苯并[d]咪唑色烯衍生物

One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives

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