Phl(OCOCF3)2-Mediated C-C Bond Formation Concomitant with a 1,2-Aryl Shift in a Metal-Free Synthesis of 3-Arylquinolin-2-ones

被引：70
|
作者：
Liu, Le [1 ]
Lu, Hang [1 ]
Wang, Hong [1 ]
Yang, Chao [1 ]
Zhang, Xiang [1 ]
Zhang-Negrerie, Daisy [1 ]
Du, Yunfei [1 ]
Zhao, Kang [1 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 12期
基金：
中国国家自然科学基金;
关键词：
ELECTROCYCLIC RING-CLOSURE; EFFICIENT SYNTHESIS; OXIDATIVE REARRANGEMENTS; DIRECT ALKYNYLATION; DIRECT ARYLATIONS; ALKENES; CYCLIZATION; FACILE; CRYPTOSANGUINOLENTINE; AMINOACETOXYLATION;
D O I：
10.1021/ol400743r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of the readily available N-methyl-N-phenylcinnamamides with phenyliodine bis(trifluoroacetate) (PIFA) In the presence of Lewis acids provides a general and efficient assembly of a variety of 3-arylquinolin-2-one compounds. This novel approach features not only metal-free oxidative C(sp(2))-C(sp(2)) bond formation but also an exclusive 1,2-aryl migration.
引用
收藏
页码：2906 / 2909
页数：4
相关论文
共 50 条
  • [1] Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study
    Liu, Le
    Zhang, Tonghuan
    Yang, Yun-Fang
    Zhang-Negrerie, Daisy
    Zhang, Xinhao
    Du, Yunfei
    Wu, Yun-Dong
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4058 - 4065
  • [2] Metal-Free Synthesis of 3-Arylquinolin-2-ones from N,2-Diarylacrylamides via Phenyliodine(III) Bis(2,2-dimethylpropanoate)-Mediated Direct Oxidative C-C Bond Formation
    Cao, Yang
    Zhao, Hui
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (22) : 3610 - 3615
  • [3] Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation
    Shi, Hao
    Guo, Tianjian
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    TETRAHEDRON, 2014, 70 (17) : 2753 - 2760
  • [4] Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)2-Mediated Oxidative C-C Bond Formation
    Lv, Jinglei
    Zhang-Negrerie, Daisy
    Deng, Jun
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03): : 1111 - 1119
  • [5] PhI(OCOCF3)2-Mediated Intramolecular Oxidative N-N Bond Formation: Metal-Free Synthesis of 1,2,4-Triazolo[1,5-a]pyridines
    Zheng, Zisheng
    Ma, Shuangyu
    Tang, Linlin
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4687 - 4693
  • [6] Synthesis of 2-(Trifluoromethyl)oxazoles from β-Monosubstituted Enamines via Phl(OCOCF3)2-Mediated Trifluoroacetoxylation and Cyclization
    Zhao, Feifei
    Liu, Xin
    Qi, Rui
    Zhang-Negrerie, Daisy
    Huang, Jianhui
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24): : 10338 - 10344
  • [7] PhI(OCOCF3)2-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione
    Yang, Chao
    Zhang, Xiang
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (10): : 5320 - 5328
  • [8] Metal-Free and Visible-Light-Promoted C-3 Thiocyanation of 2-Arylquinolin-4-ones
    Chauhan, Parul
    Ritu
    Preeti
    Kumar, Sharvan
    Jain, Nidhi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (27) : 4334 - 4340
  • [9] Metal-Free Cascade Formation of C-C and C-N Bond for the Construction of 3-Cyano-2-Pyridones with Insecticidal Properties
    Tang, Yao
    Wu, Nvjiang
    Xu, Junyu
    Zhang, Xiaopo
    Li, Youbin
    Wang, Xuesong
    MOLECULES, 2024, 29 (12):
  • [10] Metal-Free Synthesis of 2-Aryl Quinazolines via Tandem C-H/N-H Bond Functionalization
    Yuan, Feixiang
    Xie, Shihua
    Zhuo, Liang
    Wang, Lei
    Zhu, Hongjun
    CHEMISTRYSELECT, 2021, 6 (15): : 3707 - 3711
12345