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

[31] Asymmetric synthesis of poly-substituted spirocyclohexane oxindole via a squaramide catalyzed cascade Michael-Michael-aldol sequence
Sun, Qiang-Sheng
Chen, Xiao-Yang
Zhu, Hua
Lin, Hua
Sun, Xing-Wen
Lin, Guo-Qiang
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (02): : 110 - 113
[32] Asymmetric synthesis of poly-substituted spirocyclohexane oxindole via a squaramide catalyzed cascade Michael-Michael-aldol sequence
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai
200433, China
Org. Chem. Front., 2 (110-113):
[33] Recent Methods for the Synthesis of Noble-Metal-Free Hydrogen-Evolution Electrocatalysts: From Nanoscale to Sub-nanoscale
Wang, Jiong
Zhang, Hua
Wang, Xin
SMALL METHODS, 2017, 1 (06):
[34] Facile synthesis of noble-metal-free MoP as an efficient catalyst for H2 evolution from formaldehyde solution
Peng, Shaoqin
Shi, Zhengxing
Fu, Qiyue
Zeng, Wanqi
Li, Yuexiang
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2023, 48 (94) : 36750 - 36758
[35] Solid acid catalyst TS-1 zeolite-assisted solvent-free one-pot synthesis of poly-substituted 2,4,6-triaryl-pyridines
Gadekar, Sachin P.
Lande, Machhindra K.
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (05) : 3267 - 3278
[36] Synthesis of Fused Dihydropyrano(furano)pyridines via [4+2]-Cycloaddition of 5-Alkenoxy Substituted Oxazoles
Goodman, Steven N.
Mans, Douglas M.
Sisko, Joseph
Yin, Hao
ORGANIC LETTERS, 2012, 14 (06) : 1604 - 1607
[37] Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy
Wei, Hongbo
Li, Yun
Xiao, Ke
Cheng, Bin
Wang, Huifei
Hu, Lin
Zhai, Hongbin
ORGANIC LETTERS, 2015, 17 (24) : 5974 - 5977
[38] Solid acid catalyst TS-1 zeolite-assisted solvent-free one-pot synthesis of poly-substituted 2,4,6-triaryl-pyridines
Sachin P. Gadekar
Machhindra K. Lande
Research on Chemical Intermediates, 2018, 44 : 3267 - 3278
[39] Catalyst and base free aza-Michael addition reaction: Synthesis of poly-substituted 4-pyrazole based benzopyrans
Das, Tapaswini
Mohapatra, Seetaram
Mishra, Nilima Priyadarsini
Nayak, Sabita
TETRAHEDRON LETTERS, 2022, 96
[40] A Metal-Free Based New Approach to 2,4-Disubstituted Pyridines via One-Pot Sequential Reaction of Cyclic Sulfamidate Imines with β-Substituted Acroleins
Majee, Debashis
Guin, Soumitra
Biswas, Soumen
Samanta, Sampak
CHEMISTRYSELECT, 2017, 2 (12): : 3423 - 3427

← 1 2 3 4 5 →