Synthesis of 6-iodo/bromo-3-amino-2-methylquinazolin-4-(3H)-ones by direct halogenation and their Schiff base derivatives

被引:23
|
作者
Sayyed, Mudassar A. [1 ]
Mokle, Shyam S. [1 ]
Vibhute, Yeshwant B. [1 ]
机构
[1] Yeshwant Mahavidyalaya, PG Dept Chem, Nanded 431602, MS, India
关键词
6-iodo; bromo 3-amino-2-methylquinazolin-4 (3H) -ones; Schiff bases; antibacterial activity;
D O I
10.3998/ark.5550190.0007.b22
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 3-amino-2-methylquinazolin-4(3H)-one with iodine monochloride or bromine in acetic acid affords the corresponding 6-iodo / bromo 3-amino-2-methylquinazolin-4 (3H)-ones in high yields. The notable advantages of this protocol are, no need of catalyst, mild conditions, simple operation and short reaction times with high yields. New potentially active Schiff bases are prepared by condensing these 6-iodo / bromo 3-amino-2-methylquinazolin-4 (3H)-ones with different substituted aryl aldehydes. The bioactivity of the synthesized Schiff bases is studied.
引用
收藏
页码:221 / 226
页数:6
相关论文
共 50 条
  • [41] Synthesis of 5-bromo-2-substituted-4(3H)-quinazolinone
    Liu, Yizhou
    Wang, Xinying
    Jiao, Linru
    Xu, Dongdong
    Kang, Congmin
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2017, 56 (03): : 356 - 358
  • [42] Selective synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones catalyzed by Schiff base dioxomolybdenum(VI) complex
    Feng, Mengmeng
    Yan, Qingmin
    Yang, Lan
    Ye, Yanan
    Liu, Gang
    Wang, Weili
    INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 2023, 55 (03) : 119 - 128
  • [43] Synthesis, characterization and antibacterial activities of Zn(II) and Cd(II) complexes of a 3-amino-2-phenylquinazolin-4(3H)-one Schiff base
    Brahman, Dhiraj
    Sinha, Biswajit
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2014, 79 (12) : 1505 - S174
  • [44] Synthesis and biofilm inhibition studies of 2-(2-amino-6-arylpyrimidin-4-yl) quinazolin-4(3H)-ones
    Rasapalli, Sivappa
    Murphy, Zachary F.
    Sammeta, Vamshikrishna Reddy
    Golen, James A.
    Weig, Alexander W.
    Melander, Roberta J.
    Melander, Christian
    Macha, Prathyushakrishna
    Vasudev, Milana C.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (23)
  • [45] Oxidative addition of N-aminophthalimide and 3-amino-2-methylquinazolin-4(3H)-one to conjugated azocyclopentenes and azocyclohexenes
    Buchaka, SM
    Kuznetsov, MA
    Schantl, JG
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (07): : 1043 - 1051
  • [46] Synthesis of some new biologically active 2-phenyl-6-iodo-3-substituted-4(3H) quinazolinones
    Ghorab, MM
    AbdelHamide, SG
    ElHakim, AE
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 5 (02) : 115 - 120
  • [47] New 6-bromo-2-methyl-3-(Substituted Phenyl)-(3H)-quinazolin-4-Ones with Antimicrobial and Antiinflammatory activities
    Murti, Y.
    Singh, A. K.
    Pathak, D.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2011, 73 (03) : 333 - 337
  • [48] SYNTHESIS AND ANALGESIC ACTIVITY OF 4-AMINO-1,2-DIHYDRO-5-(2-HYDROXYPHENYL)-3H-PYRAZOL-3-ONES AND 5-AMINO-6-(2-HYDROXYPHENYL)PYRIMIDIN-4(3H)-ONES
    TAKAGI, K
    TANAKA, M
    MORITA, H
    OGURA, K
    ISHII, K
    NAKATA, N
    OZEKI, M
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (03) : 239 - 242
  • [49] Oxidative addition of N-aminophthalimide and 3-amino-2-methylquinazolin- 4(3H)-one to conjugated azocyclopentenes and azocyclohexenes
    Buchaka S.M.
    Kuznetsov M.A.
    Schantl J.G.
    Chemistry of Heterocyclic Compounds, 2004, 40 (7) : 895 - 902
  • [50] Synthesis and reactions of 2-methyl-3-(6-amino-2-pyridyl)-4(3H)-quinazolinone
    Strakov, AY
    Tonkikh, NN
    Palitis, EL
    Petrova, MV
    Avotinsh, FM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1999, (06): : 840 - 842