Electrochemical Cascade Cyclization Reactions of Nitrosobenzenes in Construction of Quinolines and Pyrroles

doi:10.6023/cjoc202307002

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 1021-1030.DOI: 10.6023/cjoc202307002 Previous Articles Next Articles

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亚硝基苯参与的电化学串联环化反应构建喹啉/吡咯

杨帆^a, 方婷^b, 杨桂春^a, 高梦^a^,^*()

a 湖北大学化学化工学院有机功能分子合成与应用教育部重点实验室武汉 430062
b 武汉大学化学与分子科学学院武汉 430072

收稿日期:2023-07-03 修回日期:2023-08-16 发布日期:2024-04-02
基金资助:
国家自然科学基金(22271085)

Electrochemical Cascade Cyclization Reactions of Nitrosobenzenes in Construction of Quinolines and Pyrroles

Fan Yang^a, Ting Fang^b, Guichun Yang^a, Meng Gao^a()

a Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecule, School of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062
b College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072

Received:2023-07-03 Revised:2023-08-16 Published:2024-04-02
Contact: *E-mail: drmenggao@163.com
Supported by:
National Natural Science Foundation of China(22271085)

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Abstract

A novel electrochemical cascade cyclization between nitrosobenzene and electron-deficient alkynes was developed in this work. The use of electroreduction for the activation of nitrosobenzene which highlighted the unique possibilities associated with electrochemical activation methods. This protocol represents a simple, efficient, and environmentally benign way to construct substituted quinolines and pyrroles in good yields with high selectivity.

Key words: electrosynthesis, cascade cyclization, nitrosobenzene

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Fan Yang, Ting Fang, Guichun Yang, Meng Gao. Electrochemical Cascade Cyclization Reactions of Nitrosobenzenes in Construction of Quinolines and Pyrroles[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 1021-1030.

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Fig. & Tab. 8

Scheme 1. Electrochemical cascade cyclization of nitrosobenzenes

Entry	Variation from the standard condition^a	Yield^b/%
1	None	74
2	C/Ni	38
3	C/Zn	51
4	ⁿBu₄NClO₄ instead of ⁿBu₄NI	Trace
5	ⁿBu₄NBr instead of ⁿBu₄NI	15
6	KI instead of ⁿBu₄NI	36
7	MeCN	46
8	10 mA	48
9	5 mA	37
10	No electricity	n.d.

Table 1. Reaction optimization of polysubstituted quinoline 3aa

Table 2. Synthesis of polysubstituted quinolines

Entry	Variation from the standard condition^a	Yield^b/%
1	None	63
2	Without DIPEA	32
3	No electricity	n.d.

Table 3. Reaction optimization of polysubstituted pyrroles 4aa

Table 4. Synthesis of polysubstituted pyrroles

Scheme 2. Mechanistic experiments

Figure 1. Key fragments assignment of A and B detected from the reaction solution by ESI-MS

Figure 2. Calculated Gibbs free energy profile for the construction of pyrrole ring

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亚硝基苯参与的电化学串联环化反应构建喹啉/吡咯

Electrochemical Cascade Cyclization Reactions of Nitrosobenzenes in Construction of Quinolines and Pyrroles

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References 15

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