Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction

doi:10.6023/cjoc202008028

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1241-1245.DOI: 10.6023/cjoc202008028 Previous Articles Next Articles

NOTES

利用三组分串联反应合成3-苯并[d]咪唑啉取代的吡喃并[3,2-c]色烯-2-酮衍生物

王翔¹^,^*(), 陈平¹, 支三军¹, 胡华友¹, 阚玉和¹, 唐果东¹, 张载超¹^,^*()

1 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淮安 223300

收稿日期:2020-08-16 修回日期:2020-09-28 发布日期:2020-11-19
通讯作者: 王翔, 张载超
基金资助:
国家自然科学基金(51403073); 国家自然科学基金(21601061); 江苏省高等学校自然科学研究基金(16KJB150006); 江苏省低维材料化学重点实验室开放基金(JSKC15145)

Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction

Xiang Wang¹^,^*(), Ping Chen¹, Sanjun Zhi¹, Huayou Hu¹, Yuhe Kan¹, Guodong Tang¹, Zaichao Zhang¹^,^*()

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

Received:2020-08-16 Revised:2020-09-28 Published:2020-11-19
Contact: Xiang Wang, Zaichao Zhang
About author:
* Corresponding authors. E-mail: hurricanwx@163.com;
zhangzc@hytc.edu.cn
Supported by:
National Natural Science Foundation of China(51403073); National Natural Science Foundation of China(21601061); Natural Science Foundation of the Jiangsu Higher Education Institutions of China(16KJB150006); Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials(JSKC15145)

1. cjoc202008028辅助材料.pdf(3152KB)

Abstract

Both benzimidazoles and pyranochromenes exhibit a variety of important biological activities. However, the effective preparation of compounds incorporating both pyranochromene and benzoimidazole moieties is very rare. In this paper, a HOAc-promoted three-component annulation reaction of aromatic aldehydes with 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and 4-hydroxy-2H-chromen-2-one is reported, leading to the formation of a series of 3-benzo[d]imidazol-2(3H)-ylidene substituted pyrano[3,2-c]chromen-2-ones in 58%~84% yields. The current reaction could tolerate aromatic aldehydes with diverse functional groups such as chloro, bromo, cyano, methoxy and heteroaryl aldehydes, and HOAc served as the reaction media as well as the Br?nsted acid catalyst, thereby providing an effective synthetic method for the construction ofN,O-containing heterocyles.

Key words: pyrano[3,2-c]chromen-2-one, three-component reaction, coumarins, annulation, pyrones

Cite this article

Xiang Wang, Ping Chen, Sanjun Zhi, Huayou Hu, Yuhe Kan, Guodong Tang, Zaichao Zhang. Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1241-1245.

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Entry	Solvent	Catalyst	Temp./℃	Yield^b/%
1	EtOH	None	Reflux	0
2	CH₃CN	None	Reflux	0
3	EtOH	Pyridine	Reflux	0
4^c	HOAc	None	r.t.	9
5	HOAc	None	60	42
6	HOAc	None	70	63
7	HOAc	None	80	75
8	HOAc	None	90	65
9	EtOH	HOAc	Reflux	0

Entry	Solvent	Catalyst	Temp./℃	Yield^b/%
1	EtOH	None	Reflux	0
2	CH₃CN	None	Reflux	0
3	EtOH	Pyridine	Reflux	0
4^c	HOAc	None	r.t.	9
5	HOAc	None	60	42
6	HOAc	None	70	63
7	HOAc	None	80	75
8	HOAc	None	90	65
9	EtOH	HOAc	Reflux	0

Entry	4	R¹	R²	Yield^b/%
1	4a	3-Bromophenyl	H	75
2	4b	3-Cyanophenyl	H	84
3	4c	3-Methoxyphenyl	H	61
4	4d	Pyridin-3-yl	H	58
5	4e	3,4-Dichlorophenyl	H	67
6	4f	2-Bromophenyl	H	84
7	4g	2,4-Dichlorophenyl	H	64
8	4h	4-Chlorophenyl	H	62
9	4i	4-Bromophenyl	H	65
10	4j	Phenyl	H	66
11	4k	3-Bromophenyl	CH₃	72
12	4l	3-Methoxyphenyl	CH₃	58
13	4m	Naphthalen-2-yl	H	0
14	4n	Styryl	H	0
15	4o	n-Butyl	H	0

Entry	4	R¹	R²	Yield^b/%
1	4a	3-Bromophenyl	H	75
2	4b	3-Cyanophenyl	H	84
3	4c	3-Methoxyphenyl	H	61
4	4d	Pyridin-3-yl	H	58
5	4e	3,4-Dichlorophenyl	H	67
6	4f	2-Bromophenyl	H	84
7	4g	2,4-Dichlorophenyl	H	64
8	4h	4-Chlorophenyl	H	62
9	4i	4-Bromophenyl	H	65
10	4j	Phenyl	H	66
11	4k	3-Bromophenyl	CH₃	72
12	4l	3-Methoxyphenyl	CH₃	58
13	4m	Naphthalen-2-yl	H	0
14	4n	Styryl	H	0
15	4o	n-Butyl	H	0

利用三组分串联反应合成3-苯并[d]咪唑啉取代的吡喃并[3,2-c]色烯-2-酮衍生物

Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction

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