Self-[3+2] annulation reaction of pyridinium salts: synthesis of N-indolizine-substituted pyridine-2(1H)-ones

被引：0

作者：

Cao, Yu ^{[1
,2
]}

Shi, Qiyuan ^{[3
]}

Gao, Kai ^{[4
]}

Shao, Jiaan ^{[1
]}

Zhu, Huajian ^{[1
]}

Zeng, Linghui ^{[1
]}

Zhang, Chong ^{[1
]}

Xi, Jianjun ^{[2
]}

Zhuang, Rangxiao ^{[2
]}

Zhang, Jiankang ^{[1
]}

机构：

[1] Zhejiang Univ City Coll, Sch Med, Hangzhou 310015, Peoples R China

[2] Hangzhou Xixi Hosp, Dept Pharmaceut Preparat, Hangzhou 310023, Peoples R China

[3] Hangzhou Med Coll, Sch Pharm, Hangzhou, Zhejiang, Peoples R China

[4] Zhejiang Ausun Pharmaceut Co Ltd, Taizhou, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 35期

关键词：

CATALYZED COUPLING REACTION; DERIVATIVES; ARYLATION; EFFICIENT; ARYL;

D O I：

10.1039/d2nj03232e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A self-[3+2] annulation reaction of pyridinium salts has been developed for the synthesis of N-indolizine-substituted pyridine-2(1H)-ones. This protocol was carried out under mild reaction conditions without any precious catalysts in generally moderate to good yields. Additionally, a plausible mechanism for the transformation was proposed.

引用

页码：16651 / 16655

页数：5

共 30 条

[1] Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides [J].

Brioche, Julien ;

Meyer, Christophe ;

Cossy, Janine .

ORGANIC LETTERS, 2015, 17 (11) :2800-2803

[2] Collective Synthesis of 4-Hydroxy-2-pyridone Alkaloids and Their Antiproliferation Activities [J].

Ding, Feiqing ;

Leow, Min Li ;

Ma, Jimei ;

William, Ronny ;

Liao, Hongze ;

Liu, Xue-Wei .

CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) :2548-2554

[3] Progress and Challenges in Targeted Protein Degradation for Neurodegenerative Disease Therapy [J].

Fang, Yingxu ;

Wang, Jiaxing ;

Zhao, Min ;

Zheng, Qinwen ;

Ren, Changyu ;

Zhang, Jifa ;

Wang, Yuxi .

JOURNAL OF MEDICINAL CHEMISTRY, 2022, 65 (17) :11454-11477

[4] Pharmacokinetics and pharmacodynamics of TF-505, a novel nonsteroidal 5α-reductase inhibitor, in normal subjects treated with single or multiple doses [J].

Fujita, T ;

Matsumoto, Y ;

Kimura, T ;

Yokota, S ;

Sawada, M ;

Majima, M ;

Ohtani, Y ;

Kumagai, Y .

BRITISH JOURNAL OF CLINICAL PHARMACOLOGY, 2002, 54 (03) :283-294

[5] Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis [J].

Gundersen, Lise-Lotte ;

Charnock, Colin ;

Negussie, Ayele Hailu ;

Rise, Frode ;

Teklu, Solomon .

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2007, 30 (01) :26-35

[6] Discovery of Novel Bromophenol Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer [J].

Guo, Chuanlong ;

Wang, Lijun ;

Li, Xinxue ;

Wang, Shuaiyu ;

Yu, Xuemin ;

Xu, Kuo ;

Zhao, Yue ;

Luo, Jiao ;

Li, Xiangqian ;

Jiang, Bo ;

Shi, Dayong .

JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (06) :3051-3067

[7] Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis [J].

He, Fu-Sheng ;

Ye, Shengqing ;

Wu, Jie .

ACS CATALYSIS, 2019, 9 (10) :8943-8960

[8] Synthesis of Indolizines from Pyridinium Salts and Ethyl Bromodifluoroacetate [J].

Hou, Xiaoya ;

Zhou, Sen ;

Li, Yuli ;

Guo, Minjie ;

Zhao, Wentao ;

Tang, Xiangyang ;

Wang, Guangwei .

ORGANIC LETTERS, 2020, 22 (23) :9313-9318

[9] Copper-Catalyzed N-Arylation of Tautomerizable Heterocycles with Boronic Acids and Its Application to Synthesis of Oxygenated Carbazoles [J].

Kumar, Karampoori Anil ;

Kannaboina, Prakash ;

Jaladanki, Chaitanya K. ;

Bharatam, Prasad V. ;

Das, Parthasarathi .

CHEMISTRYSELECT, 2016, 1 (03) :601-607

[10] In Vitro Characterization of MK-1439, a Novel HIV-1 Nonnucleoside Reverse Transcriptase Inhibitor [J].

Lai, Ming-Tain ;

Feng, Meizhen ;

Falgueyret, Jean-Pierre ;

Tawa, Paul ;

Witmer, Marc ;

DiStefano, Daniel ;

Li, Yuan ;

Burch, Jason ;

Sachs, Nancy ;

Lu, Meiqing ;

Cauchon, Elizabeth ;

Campeau, Louis-Charles ;

Grobler, Jay ;

Yan, Youwei ;

Ducharme, Yves ;

Cote, Bernard ;

Asante-Appiah, Ernest ;

Hazuda, Daria J. ;

Miller, Michael D. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2014, 58 (03) :1652-1663

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