One-pot synthesis of quinazolin-4(3H)-ones and fused quinazolinones by a palladium-catalyzed domino process

被引：27
|
作者：
Ren, Zhi-Lin [1 ]
Kong, Han-Han [1 ]
Lu, Wen-Ting [1 ]
Sun, Mei [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Domino reaction; Quinazolinone; Isocyanide; Carbodiimide; Palladium catalysis; AZA-WITTIG REACTION; C-H AMIDATION; ANTITUMOR EVALUATION; EFFICIENT SYNTHESIS; DERIVATIVES; ISOCYANIDE; CARBODIIMIDES; HETEROCYCLES; ACTIVATION; VASICINONE;
D O I：
10.1016/j.tet.2017.11.060
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient one-pot synthesis of quinazolin-4(3H)-ones, benzoimidazo[2,1-b]quinazolin-12(6H)-ones and imidazo[2,1-b]quinazolin-5(1H)-ones via a palladium-catalyzed domino process has been developed. The Pd-catalyzed reactions of 2-azidobenzamides 1 with isocyanides 2 produced quinazolin-4(3H)ones 4 at room temperature by a domino Pd-catalyzed cross-coupling/carbodiimide-mediated cyclization. However, as 2-azido-N-(2-bromophenyl)benzamides 1 were used under heating condition in the presence of Cs2CO3, the benzoimidazo[2,1-b]quinazolin-12(6H)-ones 5 were directly obtained by twice Pd-catalyzed domino cyclization. A domino reogioselective 5-exo-dig intramolecular cyclization reaction of alkynyl-containing azides 6 with isocyanides 2 generated imidazo[2,1-b]quinazolin-5(1H)-ones 9 in 74 -93% yields in the presence of catalyst Pd(PPh3)(4) and K2CO3. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：184 / 193
页数：10
相关论文
共 50 条
  • [41] Convenient domino synthesis of quinazolin-4(3H)-ylidene carbothioamides and carbamothioates
    Fathalla, Walid
    Pazdera, Pavel
    TETRAHEDRON, 2017, 73 (31) : 4573 - 4583
  • [42] Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3•5H2O: Investigating the role of the catalyst
    Mohammadpoor-Baltork, Iraj
    Khosropour, Ahmad R.
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Baghersad, Saeid
    Mirjafari, Arsalan
    COMPTES RENDUS CHIMIE, 2011, 14 (10) : 944 - 952
  • [43] A Simple One-Pot Synthesis of 2-Substituted Quinazolin-4(3H)-ones from 2-Nitrobenzamides by Using Sodium Dithionite
    Romero, Angel H.
    Salazar, Jose
    Lopez, Simon E.
    SYNTHESIS-STUTTGART, 2013, 45 (14): : 2043 - 2050
  • [44] Rhodium(III)-Catalyzed Synthesis of Quinazolin-4(3H)-ones with N-Methoxyamides as Synthesis Reagents
    Zhou, Guanyu
    Huang, Zhibin
    Xu, Xu
    Fang, Zhang
    Huang, Pengcheng
    Deng, Zefeng
    Li, Bao
    Zhao, Yingsheng
    SYNTHESIS-STUTTGART, 2022, 54 (14): : 3298 - 3306
  • [45] A mechanistic insight into the acid catalyzed, one-pot synthesis of isoindole-fused quinazolin 4-ones
    Mohabul A Mondal
    Sudipta Mondal
    Abdul A Khan
    Journal of Chemical Sciences, 2020, 132
  • [46] A General and Facile Synthesis of Novel Polysubstituted Quinazolin-4(3H)-ones
    Xin, Minhang
    Gao, Ying
    Xiang, Hua
    Chen, Dong
    He, Yi
    You, Qidong
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (01) : 169 - 174
  • [47] A mechanistic insight into the acid catalyzed, one-pot synthesis of isoindole-fused quinazolin 4-ones
    Mondal, Mohabul A.
    Mondal, Sudipta
    Khan, Abdul A.
    JOURNAL OF CHEMICAL SCIENCES, 2020, 132 (01)
  • [48] Domino [Pd]-Catalysis: One-Pot Synthesis of Isobenzofuran-1 (3H)-ones
    Mahendar, Lodi
    Satyanarayana, Gedu
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 7685 - 7691
  • [49] The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX
    Alam, Md Toufique
    Maiti, Saikat
    Mal, Prasenjit
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 2396 - 2403
  • [50] A NOVEL SYNTHESIS OF 2-SUBSTITUTED QUINAZOLIN-4(3H)-ONES
    SVETLIK, J
    HETEROCYCLES, 1981, 16 (08) : 1281 - 1285
12345