Silver-Catalyzed Isocyanide Insertion into N-H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives

被引:30
|
作者
Zhang, Lingjuan [1 ]
Li, Juanjuan [1 ]
Hu, Zhongyan [2 ]
Dong, Jinhuan [2 ]
Zhang, Xian-Ming [1 ]
Xu, Xianxiu [2 ]
机构
[1] Shanxi Normal Univ, Sch Chem & Mat Sci, Key Lab Magnet Mol & Magnet Informat Mat, Minist Educ, Linfen 041004, Peoples R China
[2] Shandong Normal Univ, Collaborat Innovat Ctr Functionalized Probes Chem, Coll Chem Chem Engn & Mat Sci,Minist Educ, Key Lab Mol & Nano Probes,Inst Mol & Nano Sci, Jinan 250014, Shandong, Peoples R China
关键词
silver-catalyzed; 5+1] annulation; isocyanide insertion; quinazolines; quinazoline; 3-oxides; 2-SUBSTITUTED QUINAZOLINES; 3-COMPONENT SYNTHESIS; MIGRATORY INSERTION; OXIDATIVE AMINATION; ACCESS; MULTICOMPONENT; HETEROCYCLES; ISONITRILES; ACTIVATION; ROUTE;
D O I
10.1002/adsc.201701623
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A silver-catalyzed [5+1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N-H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions.
引用
收藏
页码:1938 / 1942
页数:5
相关论文
共 50 条
  • [1] Ligand-enabled silver-catalyzed carbene insertion into the N-H bond of aliphatic and electron-rich aromatic amines
    Li, Linxuan
    Sivaguru, Paramasivam
    Han, Xinyue
    Karmakar, Swastik
    Bi, Xihe
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (07) : 1746 - 1753
  • [2] Silver-catalyzed [3+2+1] annulation of aryl amidines with benzyl isocyanide
    Lu, Xiaodong
    Xin, Xiaoyi
    Wan, Boshun
    [J]. TETRAHEDRON LETTERS, 2018, 59 (04) : 361 - 364
  • [3] A new [5+1]-annulation route to some quinazoline and fused pyrimidine derivatives
    Chattopadhyay, SK
    Dey, R
    Biswas, S
    [J]. SYNTHESIS-STUTTGART, 2005, (07): : 1083 - 1086
  • [4] Silver-catalyzed [5+1] Cyclization of 2-Vinylanilines with Benzisoxazoles
    Ge Yicong
    Nie Wanli
    Sun Guofeng
    Chen Jiaxuan
    Tian Chong
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2022, 43 (08):
  • [5] Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines
    He, Feifei
    Empel, Claire
    Koenigs, Rene M.
    [J]. ORGANIC LETTERS, 2021, 23 (17) : 6719 - 6723
  • [6] Nickel-Catalyzed Oxidative C-H/N-H Isocyanide Insertion: An Efficient Synthesis of Iminoisoindolinone Derivatives
    Hao, Wenyan
    Tian, Jun
    Li, Wu
    Shi, Renyi
    Huang, Zhiliang
    Lei, Aiwen
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (11) : 1664 - 1667
  • [7] Palladium-Catalyzed Isocyanide Insertion into the Remotely Activated N-H bond of 3-(Phenylhydrazono)oxindoles: Facile Access to Indole-N-Carboxamide Derivatives
    Soam, Pooja
    Mandal, Debasish
    Tyagi, Vikas
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (30)
  • [8] C-H and N-H Bond Annulation of Benzamides with Isonitriles Catalyzed by Cobalt(III)
    Kalsi, Deepti
    Barsu, Nagaraju
    Dahiya, Pardeep
    Sundararaju, Basker
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (17): : 3937 - 3944
  • [9] Palladium-Catalyzed [5+1] Annulation of Salicylic Acid Derivatives and Propargylic Carbonates
    Sato, Kazuya
    Ogiwara, Yohei
    Sakai, Norio
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2020, 93 (12) : 1595 - 1602
  • [10] Cobalt Catalyzed C-H and N-H Bond Annulation of Sulfonamide with Terminal and Internal Alkynes
    Kalsi, Deepti
    Sundararaju, Basker
    [J]. ORGANIC LETTERS, 2015, 17 (24) : 6118 - 6121