3-Hydroxy- and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones: synthesis and reactions with alkylating and acylating agents

被引：2
|
作者：
Khokhlov, P. S. [1 ]
Osipov, V. N. [2 ]
Roshchin, A. V. [1 ]
机构：
[1] Russian Acad Sci, NN Semenov Chem Phys Inst, Moscow 119991, Russia
[2] Russian Acad Med Sci, NN Blokhin Canc Res Ctr, Moscow 115446, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2011年 / 60卷 / 01期
关键词：
quinazolinones; 2-isothiocyanatobenzoate; hydroxylamines; cyclocondensation; alkylation; acylation; QUINAZOLINE; ALKALOIDS;
D O I：
10.1007/s11172-011-0022-1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reactions of methyl 2-isothiocyanatobenzoate with hydroxylamine and alkoxyamines afforded earlier unknown 3-hydroxy-2-sulfanylquinazolin-4(3H)-one (1a) and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones (1b, c). Base-catalyzed reactions of compound 1a with alkyl halides were not regioselective, yielding O, S-dialkylation products. In the presence of acetic acid and sodium acetate, compound 1a was alkylated only at the S atom to give 2-alkylsulfanyl-3-hydroxyquinazolin-4(3H)-ones. Selective O-acylation of compound 1a at position 3 yielded 3-acyloxy-2-sulfanylquinazolin-4(3H)-ones.
引用
收藏
页码：153 / 156
页数：4
相关论文
共 50 条
  • [41] Convenient synthesis of more complex 2-substituted 4(3H)-quinazolinones via lithiation of 2-alkyl-4(3H)-quinazolinones
    Smith, K
    El-Hiti, GA
    Abdel-Megeed, MF
    Abdo, MA
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1999, 64 (03) : 515 - 526
  • [42] A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3H)-ones
    Gupta, Radhika
    Arora, Gunjan
    Yadav, Priya
    Dixit, Ranjana
    Srivastava, Anju
    Sharma, Rakesh Kumar
    DALTON TRANSACTIONS, 2021, 50 (03) : 890 - 898
  • [43] Visible-light-promoted I2-Catalyzed synthesis of quinoxalines and 2-Benzoylquinazolin-4(3H)-ones from acetophenones
    Teng, Qing-Hu
    Qin, Wen-Jian
    Sun, Gui-Xia
    Pan, Xin-Yao
    Yang, Kun
    Wang, Kai
    Liang, Fu-Pei
    MOLECULAR CATALYSIS, 2025, 572
  • [44] Copper-Catalyzed Aerobic Oxidative Amination of sp3C-H Bonds: Efficient Synthesis of 2-Hetarylquinazolin-4(3H)-ones
    Li, Qiang
    Huang, Yao
    Chen, Tieqiao
    Zhou, Yongbo
    Xu, Qing
    Yin, Shuang-Feng
    Han, Li-Biao
    ORGANIC LETTERS, 2014, 16 (14) : 3672 - 3675
  • [45] One-Pot Synthesis of Trifluoromethylated Quinazolin-4(3H)-ones with Trifluoroacetic Acid as CF3 Source
    Almeida, Sofia
    Marti, Roger
    Vanoli, Ennio
    Abele, Stefan
    Tortoioli, Simone
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (09): : 5104 - 5113
  • [46] A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones
    Dhotare, Bhaskar B.
    Kumar, Sahil
    Wadawale, Amey
    Nayak, Sandip K.
    Kumar, Mukesh
    Goswami, Dibakar
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (45) : 21906 - 21910
  • [47] KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes
    Nomula, Vishnuvardhan
    Rao, Sadu Nageswara
    SYNTHETIC COMMUNICATIONS, 2021, 51 (17) : 2602 - 2612
  • [48] 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
  • [49] Microwave irradiation promoted reactions of benzoxazin-4-ones with primary amines. Preparation of 4(3H)-quinazolinones
    Khajavi, MS
    Sadat Hosseini, SS
    Montazari, N
    IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 1999, 18 (01): : 30 - 32
  • [50] Synthesis of Chromeno[3,4-b]pyrrol-4(3H)-ones through the Domino Cyclization of 3-Aminocoumarins with Arylglyoxal Monohydrates
    Yang, Xiaofeng
    Chen, Zhiwei
    Zhong, Weihui
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (16) : 2258 - 2265
12345