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
  • [21] Cyclisation of 3-[cyclopent-2-enyl]-4-hydroxy[1]benzopyran-2-one
    Majumdar, KC
    Choudhury, PK
    Biswas, P
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (11): : 1248 - 1252
  • [22] 4-Bromo-3-hydroxy-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)indolin-2-one
    Zhu, Song-Lei
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O307 - U2341
  • [23] Photohalogenation of 3-acetylcoumarins: Facile synthesis of 3-(2-amino-4-thiazolyl)coumarins and their conversion into 3-[(2,5-dimethylpyrrol-1-yl)thiazol-4-yl]-coumarins
    Vardhan, VA
    Rao, VR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1997, 36 (12): : 1085 - 1088
  • [24] 3-[(E)-3-(2,4-Dichlorophenyl)prop-2-enoyl]-4-hydroxy-2H-chromen-2-one
    Asad, Mohammad
    Oo, Chuan-Wei
    Osman, Hasnah
    Quah, Ching Kheng
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O3022 - U1954
  • [25] An expedient one-pot tandem method for the synthesis of 3-(2-(phenylamino)thiazol-4-yl)-2H-chromen-2-ones under green conditions
    K. Kavitha
    D. Srikrishna
    Pramod Kumar Dubey
    P. Aparna
    Journal of the Iranian Chemical Society, 2019, 16 : 1913 - 1921
  • [26] 2-(Furan-2-yl)-3-hydroxy-4H-chromen-4-one
    Wera, Michal
    Pivovarenko, Vasyl G.
    Sikorski, Artur
    Lis, Tadeusz
    Blazejowski, Jerzy
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O266 - U1714
  • [27] An expedient one-pot tandem method for the synthesis of 3-(2-(phenylamino)thiazol-4-yl)-2H-chromen-2-ones under green conditions
    Kavitha, K.
    Srikrishna, D.
    Dubey, Pramod Kumar
    Aparna, P.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (09) : 1913 - 1921
  • [28] Crystal structure of 3-(2,2-dibromoacetyl)-4-hydroxy-2H-chromen-2-one
    Brahmia, Ameni
    Ghouili, Afef
    Ben Hassen, Rached
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : 121 - +
  • [29] Synthesis, Crystal Structure and DNA Interaction Study of 3-(2-(3,5-Diphenyl-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one
    MURTAZA Madni
    SHAHID Hameed
    MUHAMMAD Naeem Ahmed
    KHAWAJA Ansar Yasin
    MUHAMMAD Nawaz Tahir
    Chinese Journal of Structural Chemistry, 2015, 34 (07) : 1013 - 1018
  • [30] Synthesis, Crystal Structure and DNA Interaction Study of 3-(2-(3,5-Diphenyl-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one
    Madni, Murtaza
    Hameed, Shahid
    Ahmed, Muhammad Naeem
    Yasin, Khawaja Ansar
    Tahir, Muhammad Nawaz
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2015, 34 (07) : 1013 - 1018