Stereoselective synthesis of alkyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H-yliden)acetates in solventless conditions

被引：6
|
作者：
Ramazani, A
Kazemizadeh, AR
Ganjeie, B
Ahmadi, E
机构：
[1] Zanjan Islamic Azad Univ, Dept Chem, Zanjan, Iran
[2] Zanjan Univ, Dept Chem, Zanjan, Iran
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2005年 / 180卷 / 11期
关键词：
1,3-thiazol; acetylenic ester; Michael addition; stereoselectivity; thiourea; X-ray single crystal structure analysis;
D O I：
10.1080/104265090930290
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Tiourea reacts with dialkyl acetylenedicarboxylates in solventless conditions to form 1:1 adducts, which undergo a cyclization reaction to produce alkyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H)-yliden)acetates in fairly good yields. The stereochemistry of the ethyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H)-yliden)acetate was established by the use of X-ray single crystal structure analysis. The reaction is completely stereoselective.
引用
收藏
页码：2569 / 2572
页数：4
相关论文
共 50 条
  • [31] Synthesis of 5-Amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)- 2,3-dihydro-1H-pyrrol-3-ones*
    Yu. M. Volovenko
    T. A. Volovnenko
    A. V. Tverdokhlebov
    I. G. Ryabokon'
    Russian Journal of Organic Chemistry, 2001, 37 : 1323 - 1329
  • [32] Aminolysis of 2-amino-5-benzylidene-1,3-thiazol-4(5H)-one in cyclic amines:: Recyclization to 2-amino-5-benzylidene-1,5-dihydro-4H-imidazol-4-one derivatives
    Ramsh, S. M.
    Medvedskii, N. L.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2007, 77 (05) : 971 - 972
  • [33] Synthesis of 4-Aryl-2-hydroxy-4-oxo-N-{4-[(1,3-thiazol-2-yl)- sulfamoyl]phenyl}but-2-eneamides
    V. L. Gein
    O. V. Bobrovskaya
    A. A. Russkikh
    N. N. Petukhova
    Russian Journal of General Chemistry, 2018, 88 : 334 - 337
  • [34] (2Z)-Methyl 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)ethanoate
    Sharif, Shahzad
    Tahir, M. Nawaz
    Khan, Islam Ullah
    Salariya, Manan Ayub
    Ahmad, Sarfraz
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1455 - U1444
  • [35] Aminolysis of 2-amino-5-benzylidene-1,3-thiazol-4(5H)-one in cyclic amines: Recyclization to 2-amino-5-benzylidene-1,5-dihydro-4H-imidazol-4-one derivatives
    S. M. Ramsh
    N. L. Medvedskii
    Russian Journal of General Chemistry, 2007, 77 : 971 - 972
  • [36] Synthesis of 5-amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)2,3-dihydro-1H-pyrrol-3-ones
    Volovenko, YM
    Volovnenko, TA
    Tverdokhlebov, AV
    Ryabokon, IG
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (09) : 1323 - 1329
  • [37] Synthesis of 4-Aryl-2-hydroxy-4-oxo-N-{4-[(1,3-thiazol-2-yl)- sulfamoyl]phenyl}but-2-eneamides
    Gein, V. L.
    Bobrovskaya, O. V.
    Russkikh, A. A.
    Petukhova, N. N.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (02) : 334 - 337
  • [38] Synthesis of (Z)-2-acyl-2-enals via retrocycloadditions of 5-acyl-4-alkyl-4H-1,3-dioxins:: Application in the total synthesis of the cytotoxin (±)-euplotin A
    Aungst, RA
    Funk, RL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) : 9455 - 9456
  • [39] SYNTHESIS OF 2-ALKYL-4H,1,3-BENZOXAZINE-4-ONES
    HANADA, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1958, 31 (09) : 1024 - 1026
  • [40] Synthesis and glycosidase inhibitory activity of novel (2-phenyl-4H-benzopyrimedo[2,1-b]-thiazol-4-yliden)acetonitrile derivatives
    Patil, Vijay S.
    Nandre, Kamalakar P.
    Ghosh, Sougata
    Rao, Vaidya Jayathirtha
    Chopade, Balu A.
    Bhosale, Sheshanath V.
    Bhosale, Sidhanath V.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (23) : 7011 - 7014
12345