Iodine promoted dual oxidative C(sp3)-H amination of 2-methyl-3-arylquinazolin-4(3H)-ones: a facile route to 1,4-diarylimidazo[1,5-a]quinazolin-5(4H)-ones

被引：13
作者：
Donthiboina, Kavitha [1 ,2 ]
Namballa, Hari Krishna [1 ,2 ]
Shaik, Siddiq Pasha [2 ]
Nanubolu, Jagadeesh Babu [3 ]
Shankaraiah, Nagula [1 ]
Kamal, Ahmed [1 ,2 ]
机构：
[1] NIPER, Dept Med Chem, Hyderabad 500037, Andhra Pradesh, India
[2] Indian Inst Chem Technol, CSIR, Dept Med Chem & Biotechnol, Hyderabad 500007, Andhra Pradesh, India
[3] Indian Inst Chem Technol, CSIR, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 10期
关键词：
C-H BONDS; METAL-FREE CONDITIONS; ONE-POT SYNTHESIS; PRACTICAL SYNTHESIS; EFFICIENT SYNTHESIS; ACRIDONE ALKALOIDS; CYCLIZATION; FUNCTIONALIZATION; QUINAZOLINES; DERIVATIVES;
D O I：
10.1039/c7ob02677c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An iodine promoted tandem oxidative condensation of benzylamines and 2-methylquinazolin-4-(3H)-ones was developed to yield imidazo[1,5-a] quinazolin-5(4H)-ones via dual C(sp(3))-H amination under metal free conditions in a greener way using molecular oxygen as a terminal oxidant. This tandem transformation provides an efficient approach to construct various functionalized imidazo[1,5-a] quinazolin-5(4H)-ones in a straightforward manner via a sequential amination-oxidation-annulation-aromatisation.
引用
收藏
页码：1720 / 1727
页数：8
相关论文
共 61 条
  • [1] Novel routes to pyrroles, indoles and carbazoles -: Applications in natural product synthesis
    Agarwal, S
    Cämmerer, S
    Filali, S
    Fröhner, W
    Knöll, J
    Krahl, MP
    Reddy, KR
    Knölker, HJ
    [J]. CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) : 1601 - 1614
  • [2] Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles
    Armstrong, Alan
    Collins, James C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) : 2282 - 2285
  • [3] Iodine-Mediated Intramolecular Electrophilic Aromatic Cyclization in Allylamines: A General Route to Synthesis of Quinolines, Pyrazolo[4,3-b]pyridines, and Thieno[3,2-b]pyridines
    Batchu, Harikrishna
    Bhattacharyya, Soumya
    Batra, Sanjay
    [J]. ORGANIC LETTERS, 2012, 14 (24) : 6330 - 6333
  • [4] STUDIES ON QUINAZOLINES .5. 2,3-DIHYDROIMIDAZO[1,2-C]QUINAZOLINE DERIVATIVES - A NOVEL CLASS OF POTENT AND SELECTIVE ALPHA(1)-ADRENOCEPTOR ANTAGONISTS AND ANTIHYPERTENSIVE AGENTS
    CHERN, JW
    TAO, PL
    YEN, MH
    LU, GY
    SHIAU, CY
    LAI, YJ
    CHIEN, SL
    CHAN, CH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (15) : 2196 - 2207
  • [5] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
    Cho, Seung Hwan
    Kim, Ji Young
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
  • [6] Catalytic C-H amination: recent progress and future directions
    Collet, Florence
    Dodd, Robert H.
    Dauban, Philippe
    [J]. CHEMICAL COMMUNICATIONS, 2009, (34) : 5061 - 5074
  • [7] Synthesis of quinazolinones and quinazolines
    Connolly, DJ
    Cusack, D
    O'Sullivan, TP
    Guiry, PJ
    [J]. TETRAHEDRON, 2005, 61 (43) : 10153 - 10202
  • [8] Hypervalent iodine reagents as a new entrance to organocatalysts
    Dohi, Toshifumi
    Kita, Yasuyuki
    [J]. CHEMICAL COMMUNICATIONS, 2009, (16) : 2073 - 2085
  • [9] A Metal-Free Amination of Benzoxazoles - The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes
    Froehr, Tanja
    Sindlinger, Christian P.
    Kloeckner, Ulrich
    Finkbeiner, Peter
    Nachtsheim, Boris J.
    [J]. ORGANIC LETTERS, 2011, 13 (14) : 3754 - 3757
  • [10] Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles
    Gonzalez, Juan F.
    Ortin, Irene
    de la Cuesta, Elena
    Carlos Menendez, J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (21) : 6902 - 6915
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