Synthesis of Poly-Substituted Pyridines via Noble-Metal-Free Cycloaddition of Ketones and Imines

被引：1

作者：

Mao, Yeting ^{[1
]}

Mao, Hong ^{[1
]}

Xu, Jiaojiao ^{[1
]}

Liu, Tianqi ^{[1
]}

Liu, Bingxin ^{[1
]}

Tan, Qitao ^{[1
]}

Ding, Chang-Hua ^{[1
]}

Xu, Bin ^{[1
,2
]}

机构：

[1] Shanghai Univ, Affiliated Nantong Hosp, Shanghai Engn Res Ctr Organ Repair,Dept Chem, Innovat Drug Res Ctr,Peoples Hosp Nantong 6, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2021年 / 16卷 / 23期

基金：

中国国家自然科学基金;

关键词：

substituted pyridine; formal [4+2] cycloaddition; ketone; imine; noble-metal-free; HIGHLY FUNCTIONALIZED PYRIDINES; BOND-CLEAVAGE; ALPHA; BETA-UNSATURATED KETOXIMES; REGIOSELECTIVE SYNTHESIS; CATALYZED CYCLIZATION; TERMINAL ALKYNES; OXIMES; CONSTRUCTION; ISOCYANIDES; INHIBITORS;

D O I：

10.1002/asia.202100983

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An eco-friendly and noble-metal-free formal [4+2] cycloaddition reaction was developed for the efficient synthesis of biologically interesting poly-substituted pyridines from easily available ketones and imines, whereby two sequential C-C bonds are formed. The given approach features a unique synthetic strategy of imines and ketones with wide substrate scope, good functional group tolerance, mild conditions and operational simplicity, which represents a more direct pathway to synthesize poly-substituted pyridines than traditional methods.

引用

页码：3905 / 3908

页数：4

共 50 条

[1] Synthesis of Hantzsch poly-substituted pyridines containing adamantyl moiety
Mina Abkar Aras
Adeleh Moshtaghi Zonouz
Monatshefte für Chemie - Chemical Monthly, 2024, 155 : 189 - 193
[2] Synthesis of Hantzsch poly-substituted pyridines containing adamantyl moiety
Aras, Mina Abkar
Zonouz, Adeleh Moshtaghi
MONATSHEFTE FUR CHEMIE, 2024, 155 (02): : 189 - 193
[3] Synthesis of Substituted Pyridines via Formal (3+3) Cycloaddition of Enamines with Unsaturated Aldehydes and Ketones
Dai, Xi-Jie
Krolikowski, Paul
Murray, James I.
Wei, Carolyn S.
Dornan, Peter K.
Rotheli, Andreas R.
Caille, Seb
Thiel, Oliver R.
Smith, Austin G.
Parsons, Andrew T.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8437 - 8444
[4] Synthesis and Characterization of a New Series of Poly-Substituted Pyridines Containing Benzimidazoles and Its Metallic Complex
Jing, Xiaobi
Bi, Xiaoxin
Wang, Qing
Wu, Lintao
Yan, Chaoguo
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (04) : 539 - 545
[5] Selective synthesis of poly-substituted fluorine-containing pyridines and dihydropyrimidines via cascade C-F bond cleavage protocol
Chen, Zixian
Zhu, Jiangtao
Xie, Haibo
Li, Shan
Wu, Yongming
Gong, Yuefa
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (16) : 5682 - 5691
[6] Synthesis of a γ-Lactam Library via Formal Cycloaddition of Imines and Substituted Succinic Anhydrides
Tan, Darlene Q.
Atherton, Amy L.
Smith, Austin J.
Soldi, Cristian
Hurley, Katherine A.
Fettinger, James C.
Shaw, Jared T.
ACS COMBINATORIAL SCIENCE, 2012, 14 (03) : 218 - 223
[7] Sulfamic Acid-Catalyzed Multicomponent One-Pot Synthesis of Poly-Substituted Pyridines and Their Antimicrobial Activity
Janardhan, B.
Vijayalaxmi, S.
Rajitha, B.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) : 1230 - 1235
[8] An Efficient Synthesis of Poly-Substituted Phenols and Pyridines from Morita-Baylis-Hillman Acetates and Diethyl Oxalacetate
Yu, Jin
Kim, Ko Hoon
Lee, Hyun Ju
Kim, Jae Nyoung
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (10): : 3027 - 3032
[9] Noble-Metal-Free Electrocatalysts for Selective Hydrogen Peroxide Generation via Oxygen Reduction Reaction
Liu, Yuepeng
Lei, Fang
Li, Tingting
Wang, Siyu
Li, Yi
CHEMISTRY-A EUROPEAN JOURNAL, 2025,
[10] Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines
Wang, Yong
Song, Li-Juan
Zhang, Xinhao
Sun, Jianwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) : 9704 - 9708

← 1 2 3 4 5 →