A metal-free aromatic cascade for the synthesis of diverse heterocycles

被引:10
作者
Schlitzer, Steven C. [1 ,2 ]
Arunprasath, Dhanarajan [1 ,2 ]
Stevens, Katelyn G. [1 ,2 ]
Sharma, Indrajeet [1 ,2 ]
机构
[1] Univ Oklahoma, Dept Chem & Biochem, 101 Stephenson Pkwy, Norman, OK 73071 USA
[2] Univ Oklahoma, Inst Nat Prod Applicat & Res Technol, 101 Stephenson Pkwy, Norman, OK 73071 USA
来源
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 07期
关键词
STEREOSELECTIVE-SYNTHESIS; ELECTROCYCLIC REACTIONS; KETENES; REACTIVITY; CATALYSIS; ANALOGS; YLIDES; ACCESS; STILLE;
D O I
10.1039/c9qo01336a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free aromatic cascade has been developed for the synthesis of diverse heterocycles from readily accessible hydroxy/aminochalcones and acid/alkyl halides. The cascade is initiated by a base-mediated intramolecular aldol cyclization/dehydration sequence to provide a triene, which sets the stage for a 6 pi-electrocyclization/oxidative aromatization to access diverse heterocyclic scaffolds.
引用
收藏
页码:913 / 918
页数:6
相关论文
共 50 条
  • [1] Transition Metal-Free Synthesis of Carbo- and Heterocycles via Reaction of Alkynes with Organylchalcogenides
    Zeni, Gilson
    Godoi, Benhur
    Jurinic, Carla K.
    Belladona, Andrei L.
    Schumacher, Ricardo F.
    CHEMICAL RECORD, 2021, 21 (06) : 1342 - 1357
  • [2] Synthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process
    Wei, Kai
    Sun, Yu-Cui
    Li, Rui
    Zhao, Jing-Feng
    Chen, Wen
    Zhang, Hongbin
    ORGANIC LETTERS, 2021, 23 (17) : 6669 - 6673
  • [3] One-pot synthesis of diverse isoindolobenzoxazinone and isoindoloquinazolinone derivatives through a transition metal-free cascade cyclization
    Xu, Xin-Ming
    Shi, Ran
    Li, Wenzhong
    Zhang, Xuesi
    Chen, Sen
    Wang, Zu-Li
    Wang, Xiangmin
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1281
  • [4] Recent advances in the transition metal-free synthesis of heterocycles from α,β-unsaturated ketones
    Ashitha, Kizhakkan Thiruthi
    Krishna, Ajay M. S.
    Basavaraja, D.
    Somappa, Sasidhar B.
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5306 - 5358
  • [5] Metal-free radical cascade chloromethylation of unactivated alkenes: synthesis of polychloro-substituted indolines
    Pan, Changduo
    Gao, Du
    Yang, Zhenkun
    Wu, Chao
    Yu, Jin-Tao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (32) : 5752 - 5755
  • [6] Metal-Free Catalytic Aromatic C-H Borylation
    Zhang, Hua
    Wang, Li
    SYNLETT, 2020, 31 (19) : 1857 - 1861
  • [7] Mild and metal-free oxy- and amino-fluorination for the synthesis of fluorinated heterocycles
    Parmar, Dixit
    Rueping, Magnus
    CHEMICAL COMMUNICATIONS, 2014, 50 (90) : 13928 - 13931
  • [8] Transition metal-free one-pot synthesis of nitrogen-containing heterocycles
    Kumari, Simpal
    Kishore, Dharma
    Paliwal, Sarvesh
    Chauhan, Rajani
    Dwivedi, Jaya
    Mishra, Aakanksha
    MOLECULAR DIVERSITY, 2016, 20 (01) : 185 - 232
  • [9] PIII-Mediated intramolecular cyclopropanation and metal-free synthesis of cyclopropane-fused heterocycles
    Zhang, Jiayong
    Hao, Jiahang
    Huang, Zhiqiang
    Han, Jie
    He, Zhengjie
    CHEMICAL COMMUNICATIONS, 2020, 56 (70) : 10251 - 10254
  • [10] Metal-free Dehydrogenative Isoquinolone Synthesis
    Jin, Rongwei
    Patureau, Frederic W.
    CHEMCATCHEM, 2015, 7 (02) : 223 - 225