Ag-Catalyzed Cyclization of Ugi-Azide Adducts for the Synthesis of Fully Substituted Fused Pyrroles

doi:10.6023/cjoc202502025

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 2128-2138.DOI: 10.6023/cjoc202502025 Previous Articles Next Articles

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Ugi-Azide/银催化环化反应合成多取代稠合吡咯

罗树珍^a^,^†, 汤全^a^,^†, 龙天宇^a^,^b^,^†, 吴昊^a, 孔晗晗^a^,^*(), 任志林^c^,^*(), 阳青青^a, 王龙^a^,^d^,^*()

^a 三峡大学材料与化工学院无机非金属晶态与能量转换材料重点实验室湖北宜昌 443002
^b 三峡大学水利与环境学院湖北宜昌 443002
^c 湖北文理学院食品科学与化学工程学院湖北襄阳 441053
^d 湖北三峡实验室湖北宜昌 443007

收稿日期:2025-02-20 修回日期:2025-04-02 发布日期:2025-04-16
通讯作者: 孔晗晗, 任志林, 王龙
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22301160); 国家自然科学基金(21702121); 国家自然科学基金(21602123); 高等学校学科创新引智计划（111计划）(D20015); 湖北省自然科学基金(2025AFA116); 湖北省自然科学基金(2025AFD270); 湖北省自然科学基金(2024AFB727); 湖北省自然科学基金(2023AFB026); 中国博士后科学基金(2023M742043); 湖北三峡实验室基金(SC240014); 湖北三峡实验室基金(SC232008); 湖北三峡实验室基金(SC213008); 天然产物研究与利用湖北省重点实验室基金(2024NPRD08); 天然产物研究与利用湖北省重点实验室基金(2022NPRD04)

Ag-Catalyzed Cyclization of Ugi-Azide Adducts for the Synthesis of Fully Substituted Fused Pyrroles

Shuzhen Luo^a^,^†, Quan Tang^a^,^†, Tianyu Long^a^,^b^,^†, Hao Wu^a, Han-Han Kong^a^,^*(), Zhilin Ren^c^,^*(), Qing-Qing Yang^a, Long Wang^a^,^d^,^*()

^a Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
^b College of Hydraulic and Environmental Engineering, China Three Gorges University, Yichang, Hubei 443002
^c School of Food Science and Chemical Engineering, Hubei University of Arts and Science, Xiangyang, Hubei 441053
^d Hubei Three Gorges Laboratory, Yichang, Hubei 443007

Received:2025-02-20 Revised:2025-04-02 Published:2025-04-16
Contact: Han-Han Kong, Zhilin Ren, Long Wang
About author:
^†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22301160); National Natural Science Foundation of China(21702121); National Natural Science Foundation of China(21602123); Programme of Introducing Talents of Discipline to Universities (111 Project)(D20015); Natural Science Foundation of Hubei Province(2025AFA116); Natural Science Foundation of Hubei Province(2025AFD270); Natural Science Foundation of Hubei Province(2024AFB727); Natural Science Foundation of Hubei Province(2023AFB026); China Postdoctoral Science Foundation(2023M742043); Hubei Three Gorges Laboratory Foundation(SC240014); Hubei Three Gorges Laboratory Foundation(SC232008); Hubei Three Gorges Laboratory Foundation(SC213008); Foundation of Hubei Key Laboratory of Natural Products Research and Development(2024NPRD08); Foundation of Hubei Key Laboratory of Natural Products Research and Development(2022NPRD04)

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Abstract

An efficient and concise approach to all-carbon substituted pyrrole skeletons via Ag-catalyzed tandem cyclization reactions is reported. In this protocol, the Ugi-Azide reaction of readily available enynals, primary amines, isocyanides, and TMSN₃ was designed for the preparation of alkynyl allylic amine derivatives, followed by AgNO₃-catalyzed cyclization at room temperature, leading to fully substituted fused pyrroles. The reaction features mild reaction conditions, high atom economy, and good functional group tolerance.

Key words: fully substituted fused pyrroles, cyclization, Ugi-Azide, Ag-catalyzed

Cite this article

Shuzhen Luo, Quan Tang, Tianyu Long, Hao Wu, Han-Han Kong, Zhilin Ren, Qing-Qing Yang, Long Wang. Ag-Catalyzed Cyclization of Ugi-Azide Adducts for the Synthesis of Fully Substituted Fused Pyrroles[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2128-2138.

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Entry	Catalyst (mol%)	Solvent	Yield^b/%	Entry	Catalyst (mol%)	Solvent
1	PdCl₂ (10)	CH₃CN	19	9	None	CH₃CN	9
2	Pd(OAc)₂ (10)	CH₃CN	62	10^c^,^d	AgNO₃ (10)	CH₃CN	93
3	CuI (10)	CH₃CN	Trace	11^c^,^d^,^e	AgNO₃ (10)	CH₃CN	93
4	CuCl₂ (10)	CH₃CN	32	12^c^,^d^,^e	AgNO₃ (10)	CH₃OH	91
5	AgNO₃ (10)	CH₃CN	91	13^c^,^d^,^e	AgNO₃ (10)	THF	90
6	AgOAc (10)	CH₃CN	70	14^c^,^d^,^e	AgNO₃ (5)	CH₃CN	88
7	AgTFA (10)	CH₃CN	73	15^c^,^d^,^e	AgNO₃ (20)	CH₃CN	93
8	Ag₂CO₃ (10)	CH₃CN	31

Entry	Catalyst (mol%)	Solvent	Yield^b/%	Entry	Catalyst (mol%)	Solvent
1	PdCl₂ (10)	CH₃CN	19	9	None	CH₃CN	9
2	Pd(OAc)₂ (10)	CH₃CN	62	10^c^,^d	AgNO₃ (10)	CH₃CN	93
3	CuI (10)	CH₃CN	Trace	11^c^,^d^,^e	AgNO₃ (10)	CH₃CN	93
4	CuCl₂ (10)	CH₃CN	32	12^c^,^d^,^e	AgNO₃ (10)	CH₃OH	91
5	AgNO₃ (10)	CH₃CN	91	13^c^,^d^,^e	AgNO₃ (10)	THF	90
6	AgOAc (10)	CH₃CN	70	14^c^,^d^,^e	AgNO₃ (5)	CH₃CN	88
7	AgTFA (10)	CH₃CN	73	15^c^,^d^,^e	AgNO₃ (20)	CH₃CN	93
8	Ag₂CO₃ (10)	CH₃CN	31

Ugi-Azide/银催化环化反应合成多取代稠合吡咯

Ag-Catalyzed Cyclization of Ugi-Azide Adducts for the Synthesis of Fully Substituted Fused Pyrroles

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