Metal-free annulation of β-acylamino ketones: facile access to spirooxazolines and oxazolines via oxidative C-O bond formation

被引:23
|
作者
Chavan, Santosh S. [1 ]
Rupanawar, Bapurao D. [1 ]
Kamble, Rohit B. [1 ]
Shelke, Anil M. [1 ]
Suryavanshi, Gurunath [1 ]
机构
[1] CSIR, Chem Engn & Proc Dev Div, Natl Chem Lab, Dr Homi Bhaba Rd, Pune 411008, Maharashtra, India
来源
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 04期
关键词
ONE-POT SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; CYCLIZATION; EFFICIENT; NITRILES; ESTERS; CONVERSION; CHEMISTRY; CATALYSIS; ALDEHYDES;
D O I
10.1039/c7qo00783c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free annulation reaction of beta-acylamino ketone derivatives has been reported for the synthesis of a group of functionalized spirooxazolines and oxazolines in good to excellent yields. The reaction proceeds via phenyliodine(III) diacetate (PIDA)-mediated oxidative C-O bond formation in the presence of BF3-OEt2. The mild reaction conditions, broad substrate scope, simple execution and synthetic potential of the products make this novel protocol very attractive.
引用
收藏
页码:544 / 548
页数:5
相关论文
共 50 条
  • [1] Facile Access to Chiral Ketones through Metal-Free Oxidative C?C Bond Cleavage of Aldehydes by O2
    Tiwari, Bhoopendra
    Zhang, Junmin
    Chi, Yonggui Robin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) : 1911 - 1914
  • [2] Metal-and Base-Free Oxidative Cleavage of C(O)-C Bond in Ketones to Access Esters
    Zhou, Zhengrui
    Pi, Shaofeng
    Wang, Ru
    CHEMISTRYSELECT, 2022, 7 (29):
  • [3] Electrochemical C-O Bond Formation: Facile Access to Aromatic Lactones
    Tao, Xiang-Zhang
    Dai, Jian-Jun
    Zhou, Jie
    Xu, Jun
    Xu, Hua-Jian
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (27) : 6932 - 6935
  • [4] A transition metal-free approach towards synthesis of -carboline tethered 1,3,4-oxadiazoles via oxidative C-O bond formation
    Singh, Dharmender
    Tiwari, Sandip Kumar
    Singh, Virender
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (01) : 93 - 102
  • [5] A Metal-Free Tandem C-C/C-O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans
    Reddy, Chada Raji
    Reddy, Motatipally Damoder
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) : 106 - 116
  • [6] Metal-Free Radical Oxidative Annulation of Ynones with Alkanes To Access Indenones
    Pan, Changduo
    Huang, Bifan
    Hu, Weiming
    Feng, Xiaomei
    Yu, Jin-Tao
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05) : 2087 - 2093
  • [7] Metal-Free and Additive-Free Synthesis of Imides and Nitriles from Ketones via Oxidative of C(O)-C Bonds
    Liu, Xixi
    Qin, Jingzhong
    Dai, Wen
    Zhu, Zhihua
    Zhou, Peng
    Wang, Yanxin
    Nie, Jiabao
    Yang, Yingkui
    Zhang, Zehui
    ACS CATALYSIS, 2022, 12 (21) : 13300 - 13311
  • [8] I2-Mediated Oxidative C-O Bond Formation for the Synthesis of Isoxazoles
    Hou, Jiao
    Zhang, Xinting
    Yu, Wenquan
    Chang, Junbiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (12) : 3236 - 3241
  • [9] Metal free C-O bond cleavage: a new strategy for the synthesis of substituted oxazoles
    Li, Shengwang
    Liu, Guiqin
    Zhang, Zheyan
    Chen, Ruiling
    Tian, Haiying
    Wang, Huifeng
    Chen, Xiuling
    RSC ADVANCES, 2024, 14 (38) : 28210 - 28214
  • [10] Facile access to trifluoromethyl propargyl alcohol by metal-free transfer hydrogenation and cyanation of alkynyl ketones
    Ajitrao Kisan, Devadkar
    Paul, Ishita
    Dey, Soumyadip
    Sau, Abhijit
    Panda, Tarun K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 23 (01) : 197 - 201