NH4I-CATALYZED FORMAL [4+2] CYCLOADDITION OF α,β-UNSATURATED O-ACETYL OXIME WITH ALKYL PYRUVATE FOR RAPID SUBSTITUTED PYRIDINE FORMATION

被引：1
|
作者：
Cheng, Dong [1 ]
Meng, Xiangzhen [1 ]
Wang, Shuailu [1 ]
Zhao, Xuan [1 ]
Chen, Jingwen [1 ]
机构：
[1] Chaohu Coll, Dept Chem & Mat Engn, Chaohu 238000, Anhui, Peoples R China
来源：
HETEROCYCLES | 2022年 / 104卷 / 08期
关键词：
CYCLIC SULFAMIDATE IMINES; POLYSUBSTITUTED PYRIDINES; ACETATES; FUNCTIONALIZATION; DERIVATIVES; ANNULATION; CLEAVAGE; ACCESS;
D O I：
10.3987/COM-22-14688
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile synthetic method to substituted pyridines has been developed via the NH4I-catalyzed [4+2] cycloaddition of readily available oxime acetates with alkyl pyruvate. This process involves N-O bond cleavages and C-C bond formations to furnish substituted pyridines under redox-neutral conditions. The reaction features mild conditions and high functional-groups compatibility.
引用
收藏
页码：1435 / 1446
页数：12
相关论文
共 23 条
  • [1] Copper/amine-catalyzed formal regioselective [3+2] cycloaddition of an α,β-unsaturated O-acetyl oxime with enals
    Xie, Ying
    Li, Yulong
    Chen, Xun
    Liu, Yingle
    Zhang, Wei
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1698 - 1701
  • [2] Cinchona alkaloid-catalyzed formal [4+2] cycloaddition of allenoates and a, β-unsaturated trifluoromethylketones
    Kasten, Kevin
    Smith, Andrew
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [3] Atroposelective Arene Formation by Carbene-Catalyzed Formal [4+2] Cycloaddition
    Xu, Ke
    Li, Wenchang
    Zhu, Shaoheng
    Zhu, Tingshun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (49) : 17625 - 17630
  • [4] NH4I-Triggered [4+2] Annulation of α,β-Unsaturated Ketoxime Acetates with N-Acetyl Enamides for the Synthesis of Pyridines
    Duan, Jindian
    Zhang, Lei
    Xu, Gaochen
    Chen, Heming
    Ding, Xiaojuan
    Mao, Yiyang
    Rong, Binsen
    Zhu, Ning
    Guo, Kai
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 8157 - 8165
  • [5] Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives
    Suarez-Rodriguez, Tatiana
    Suarez-Sobrino, angel L.
    Ballesteros, Alfredo
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (51) : 13079 - 13084
  • [6] Formal [4+2] Cycloaddition of Alkoxy-Substituted Donor-Acceptor Cyclobutanes and Aldehydes Catalyzed by Yb(OTf)3
    Moustafa, Mahmoud M. Abd Rabo
    Stevens, Andrew C.
    Machin, Ben P.
    Pagenkopf, Brian L.
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 4736 - 4738
  • [7] Enantioselective Indium(I)/Chiral Phosphoric Acid-catalyzed [4+2] Cycloaddition of Simple Olefin and β , γ-Unsaturated α-Keto Esters
    Li Sujia
    Lu Jian
    Luo Sanzhong
    [J]. ACTA CHIMICA SINICA, 2018, 76 (11) : 869 - 873
  • [8] Synthesis of Densely Substituted Pyridine Derivatives from 1-Methyl-1,3-(ar)enynes and Nitriles by a Formal [4+2] Cycloaddition Reaction
    He, Dandan
    Wang, Bowen
    Duan, Kanghui
    Zhou, Yang
    Li, Meng
    Jiang, Huanfeng
    Wu, Wanqing
    [J]. ORGANIC LETTERS, 2022, 24 (06) : 1292 - 1297
  • [9] Ruthenium-Catalyzed Formal Dehydrative [4+2] Cycloaddition of Enamides and Alkynes for the Synthesis of Highly Substituted Pyridines: Reaction Development and Mechanistic Study
    Wu, Jicheng
    Xu, Wenbo
    Yu, Zhi-Xiang
    Wang, Jian
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) : 9489 - 9496
  • [10] NHC-Catalyzed Efficient Syntheses of Isoquinolinones or Isochromanones through Formal [4+2] Cycloaddition of o-Quinodimethanes with Acylhydrazones or Ketones
    Hu, Yong
    Pan, Di
    Cong, Lin
    Yao, Yibiao
    Yu, Chenxia
    Li, Tuanjie
    Yao, Changsheng
    [J]. CHEMISTRYSELECT, 2018, 3 (06): : 1708 - 1712
123