Hantzsch reaction of 3-(2-bromoacetyl)-4-hydroxy-chromen-2-one. Synthesis of 3-(thiazol-4-yl)-4-hydroxy coumarines

被引:25
|
作者
Sukdolak, S [1 ]
Soluji, S
Manojlovic, N
Vukovic, N
Krstic, L
机构
[1] Univ Kragujevac, Fac Sci, Dept Chem, YU-34000 Kragujevac, Serbia Monteneg, Serbia
[2] ICTM, Ctr Chem, YU-11001 Belgrade, Serbia Monteneg, Serbia
关键词
D O I
10.1002/jhet.5570410418
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Acetyl-4-hydroxy-chromen-2-one (1) was brominated with phenyltrimethylammonium tribromide to afford 3-(2-bromoacetyl)-4-hydroxy-chromen-2-one (2) whose reactions with thiourea, thioacetamide and ammonium dithiocarbamate gave respectively 3 - (2-amino-thiazol-4-yl)-4-hydroxy-, 4-hydroxy-3-(2-phenyl-thiazol-4-yl)- and 4-hydroxy-3-(2-mercapto-thiazol-4-yl)chromen-2-one. In a similar manner, compound 2 was treated with four 1-substituted-2-thioureas and thiobenzamide to give the corresponding 4-hydroxy-3-(thiazol-4-yl)-chromen-2-one derivatives.
引用
收藏
页码:593 / 596
页数:4
相关论文
共 50 条
  • [1] HANTZSCH REACTION OF 3-(2-BROMOACETYL)TROPOLONE - SYNTHESIS OF 3-(4-THIAZOLYL)TROPOLONES
    QIAN, CY
    JIN, ZT
    YIN, BZ
    IMAFUKU, K
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (03) : 601 - 604
  • [2] (E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one
    Abonia, Rodrigo
    Gutierrez, Luisa
    Quiroga, Jairo
    Insuasty, Braulio
    MOLBANK, 2018, (03)
  • [3] Facile one-pot synthesis of 3-{2-[5-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-ones via a three-component reaction
    Rao, V. Rajeswar
    Kumar, P. Vijaya
    SYNTHETIC COMMUNICATIONS, 2006, 36 (15) : 2157 - 2161
  • [4] 3-{2-[2-(Diphenylmethylene)hydrazinyl]thiazol-4-yl}-2H-chromen-2-one
    Arshad, Afsheen
    Osman, Hasnah
    Chan, Kit Lam
    Yeap, Chin Sing
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1788 - U448
  • [5] Synthesis of new 3-(2-aminothiazol-4-yl)-4-hydroxy-2H-chromen-2-one derivatives
    Sukdolak, S.
    Vukovic, N.
    Solujic, S.
    Milosev, M.
    Manojlovic, N.
    Krstic, L. J.
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2006, 71 (06) : 581 - 585
  • [6] Multicomponent protocol for the synthesis of substituted methyl 3-(3-hydroxy-4-oxo-4H-chromen-2-yl)propanoates from 3-hydroxy-4H-chromen-4-one
    Komogortsev, Andrey N.
    Melekhina, Valeriya G.
    Lichitsky, Boris V.
    SYNTHETIC COMMUNICATIONS, 2022, 52 (16) : 1664 - 1671
  • [7] Synthesis and in Vitro Study of Novel Bis-[3-(2-arylmethylidenimino-1,3-thiazol-4-yl)-4-hydroxy-2H-chromen-2-one-6-yl]methane and Bis-[3-(2-arylidenhydrazo-1,3-thiazol-4-yl)-4-hydroxy-2H-chromen-2-one-6-yl]methane as Potential Antimicrobial Agents
    Raghu, M.
    Nagaraj, A.
    Reddy, Ch. Sanjeeva
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (02) : 261 - 267
  • [8] Synthesis of 3-(2-Substituted thiazol-4-yl)guaiazulenes and Their Antibacterial Activity
    Wang, Daolin
    Han, Shan
    Huang, Xiaodong
    Gu, Zheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (10) : 1659 - 1663
  • [9] 3-(2-Bromoacetyl)-6-fluoro-2H-chromen-2-one
    HarishKumar, H. N.
    Mahapatra, Sudarshan
    Venugopala, K. N.
    Mahadevan, Kittappa Mariswamy
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2264 - U2010
  • [10] (2Z)-3-(5-hydroxy-4-oxo-4H-chromen-3-yl)acrylonitrile
    Araya-Maturana, R
    Heredia-Moya, J
    Pessoa-Mahana, H
    Weiss-López, B
    Muñoz, JC
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O237 - O239