Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation

被引：16
|
作者：
Ramanathan, Mani [1 ]
Hsu, Ming-Tsung [1 ]
Liu, Shiuh-Tzung [1 ]
机构：
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
来源：
TETRAHEDRON | 2019年 / 75卷 / 06期
关键词：
Quinazolinone; Diazonium; Nitrilium; Nitrile; Annulation; CHEMISTRY; QUINAZOLINONES; AFLOQUALONE; INHIBITORS; POTENT;
D O I：
10.1016/j.tet.2018.12.065
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码：791 / 796
页数：6
相关论文
共 50 条
  • [41] Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α-keto acids with 2-aminobenzamides
    Tian, Qing
    Zhang, Jinli
    Xu, Liang
    Wei, Yu
    MOLECULAR CATALYSIS, 2021, 500
  • [42] A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines
    Abe, Takumi
    Kida, Koshiro
    Yamada, Koji
    CHEMICAL COMMUNICATIONS, 2017, 53 (31) : 4362 - 4365
  • [43] An Easy Entry into 2-Halo-3-aryl-4(3H)-quinazoliniminium Halides from Heteroenyne-allenes
    Naganaboina, Vijaya Kumar
    Chandra, Kusum Lata
    Desper, John
    Rayat, Sundeep
    ORGANIC LETTERS, 2011, 13 (14) : 3718 - 3721
  • [44] Rhodium(iii)-catalyzed annulation of 3-arylquinazolinones with alkynes via double C-H activation: an efficient route for quinolino[2,1-b]quinazolinones
    Huang, Jian
    Chen, Wei
    Liang, Jiazhi
    Yang, Qin
    Deng, Zhihong
    Song, Zhibin
    Peng, Yiyuan
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24): : 6837 - 6844
  • [45] Highly diastereoselective annulation of 2-substituted 3-nitro-2H-chromenes with hemicurcuminoids and curcuminoids via a double and triple Michael reaction cascade
    Zimnitskiy, Nikolay S.
    Barkov, Alexey Yu.
    Kochnev, Ivan A.
    Kutyashev, Igor B.
    Korotaev, Vladislav Yu.
    Sosnovskikh, Vyacheslav Ya.
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (33) : 16047 - 16057
  • [46] Synthesis and In-Vitro Antitumor Activity of Selected 7-Fluoro-6-(4-methyl-1-piperazinyl)-2-(thiosubstituted)-4(3H)-quinazolinones
    Abdel-Jalil, Raid J.
    Al-Momani, Ehab
    Tahtamooni, Lubna
    Machulla, H. -Juergen
    Voelter, Wolfgang
    LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (05) : 360 - 366
  • [47] Synthesis of acetyl deoxyvasicinone analogues from 2-(4-oxopentyl) quinazolin-4(3H)-ones via linear cyclizations
    Saebang, Yotsakorn
    Rukachaisirikul, Vatcharin
    Kaeobamrung, Juthanat
    TETRAHEDRON LETTERS, 2023, 121
  • [48] Polyphosphoric Acid Esters Promoted Synthesis of Quinazolin-4(3H)-imines from 2-Aminobenzonitrile
    Kilimciler, Natalia B.
    Palavecino, Nicolas M.
    Gruber, Nadia
    Vega, Daniel R.
    Orelli, Liliana R.
    Diaz, Jimena E.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (19) : 13807 - 13817
  • [49] Synthesis of 2-Methyl-3-aryl-7-(5,5-dimethyl-3-one-1-cyclohexenyl-1-yl)-formyloxy-4(3H)-quinazolinones
    Luo, TJ
    Li, ZM
    Zhao, WG
    Fan, ZJ
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (10) : 741 - 745
  • [50] Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds
    Thorat, Vijaykumar H.
    Upadhyay, Nitinkumar Satyadev
    Murakami, Masahiro
    Cheng, Chien-Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (02) : 284 - 289
12345