A convenient one pot preparation of 4-thiazolidinones from enaminolactones

被引：0
作者：
Bouzroura, Samia [1 ]
Bentarzi, Yamina [1 ]
Kaoua, Rachedine [1 ]
Nedjar-Kolli, Bellara [1 ]
Poulain-Martini, Sophie [2 ]
Dunach, Elisabet [2 ]
机构：
[1] Houari Boumediene Univ Sci & Technol, Lab Appl Organ Chem, Algiers, Algeria
[2] Sophia Antipolis Univ, Lab Bioact Mol & Arums Sci, UMR 6001, CNRS, Nice, France
来源：
ORGANIC COMMUNICATIONS | 2010年 / 3卷 / 01期
关键词：
Pyrones; tetronic acid; thiosemicarbazides; enaminones; thiazolidinones;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enaminones 3 and 4, precursors of 4-thiazolidinones, were prepared by condensing tetronic acid (1a) and 4-hydroxy 6-methyl pyrone (1b) respectively with thiosemicarbazide derivatives 2 in refluxing ethanol. The 4-thiazolidinones 6, 7 derivatives were obtained by reacting compounds 3 or 4 with ethyl 2-bromo propionate 5 in the presence of anhydrous sodium acetate in ethalonic medium. Similarly, 9 products were synthesized by action of benzyl 2-bromo acetate 8 on 3.
引用
收藏
页码：8 / 14
页数：7
相关论文
共 47 条
  • [41] Highly Efficient One-Pot Synthesis of 2,4,5-Trisubstituted 3(2H)-Furanones Utilizing a Au(I)-Catalyzed Oxidation/Pinacol Rearrangement/anti-Michael Cascade
    Wu, Yanbin
    Zang, Shuang
    Ren, Hang
    Wang, Lingyao
    Kong, Lichun
    Zheng, Jianfeng
    Li, Jun
    ORGANIC LETTERS, 2024, 26 (36) : 7656 - 7660
  • [42] Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution
    Pankova, Alena S.
    Golubev, Pavel R.
    Khlebnikov, Alexander F.
    Ivanov, Alexander Yu.
    Kuznetsov, Mikhail A.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2563 - 2569
  • [43] 1,2,3,9-Tetrahydro-4H-carbazol-4-one and 8,9-Dihydropyrido-[1,2-a]indol-6(7H)-one from 1H-Indole-2-butanoic Acid
    Bunce, Richard A.
    Nammalwar, Baskar
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (02) : 172 - 177
  • [44] One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3- (methylthio)acrylonitriles and Benzyl Carbamate
    Saraiah, Bonagiri
    Gautam, Vibha
    Acharya, Anand
    Pasha, Mohamed Afzal
    Ila, Hiriyakkanavar
    ACS OMEGA, 2018, 3 (07): : 8355 - 8364
  • [45] Copper-catalyzed one-pot domino reactions via C-H bond activation: synthesis of 3-aroylquinolines from 2-aminobenzylalcohols and propiophenones under metal-organic framework catalysis
    Ha V Dang
    Hoang T B Le
    Loan T B Tran
    Hiep Q Ha
    Ha V Le
    Nam T S Phan
    RSC ADVANCES, 2018, 8 (55): : 31455 - 31464
  • [46] Cationic organotin cluster [t-Bu2Sn(OH)(H2O)]22+2OTf--catalyzed one-pot three-component syntheses of 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in water
    Wang, Hongshe
    Zhao, Weixing
    Du, Juan
    Wei, Fenyan
    Chen, Qi
    Wang, Xiaomei
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (10)
  • [47] Synthesis of 8,10-disubstituted-triazoloperimidines from (E)-3-(dimethylamino)-1-(8-phenyl-8H-[1,2,4] triazolo[ 4,3-a] perimidin-10-yl) prop-2-en-1-one and their Antimicrobial Activity
    Masaret, Ghada S.
    Farghaly, Thoraya A.
    CURRENT ORGANIC SYNTHESIS, 2018, 15 (01) : 126 - 136
12345