Efficient synthetic procedure to new 2-imino-1,3-thiazolines and thiazolidin-4-ones promoted by acetonitrile electrogenerated base

被引:14
作者
Haouas, Beya [1 ]
Sbei, Najwa [1 ]
Ayari, Hana [1 ]
Benkhoud, M. Lamine [1 ]
Batanero, Belen [2 ,3 ]
机构
[1] Univ Tunis El Manar, Fac Sci, Lab Chim Analyt & Electrochim, Tunis 2092, Tunisia
[2] Univ Alcala De Henares, Dept Organ Chem, Alcala De Henares 28871, Madrid, Spain
[3] Univ Alcala De Henares, Inst Invest Quim Andres M del Rio IQAR, Alcala De Henares 28871, Madrid, Spain
关键词
ONE-POT SYNTHESIS; DERIVATIVES; THIAZOLIDINE-2,4-DIONES; 4-THIAZOLIDINONES; CYCLIZATION; FACILE; DESIGN; AGENTS; ACIDS;
D O I
10.1039/c8nj01992d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and convenient strategy is described for the regioselective conversion of N,N-disubstituted thioureas and 1,2-dielectrophiles into the highly biologically valuable 2-imino-thiazoline and 2-imino thiazolidine-4-one derivatives. The synthesis proceeds through a process with good yield promoted by an electrogenerated base (EGB) obtained with high current efficiency.
引用
收藏
页码:11776 / 11781
页数:6
相关论文
共 42 条
[1]  
Alireza B., 2017, BIOORG MED CHEM LETT, V27, P228
[2]   Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes [J].
Anitha, Mandala ;
Swamy, K. C. Kumara .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (03) :402-413
[3]   Thiazolidine-2,4-diones as multi-targeted scaffold in medicinal chemistry: Potential anticancer agents [J].
Asati, Vivek ;
Mahapatra, Debarshi Kar ;
Bharti, Sanjay K. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 :814-833
[4]   Preparation of 2,6-dimethyl-4-arylpyridine-3,5-dicarbonitrile:: A paired electrosynthesis [J].
Batanero, B ;
Barba, F ;
Martín, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2369-2371
[5]   Room temperature ring-opening cyclization reactions of 2-vinylaziridines with isocyanates, carbodiimides, and isothiocyanates catalyzed by [Pd(OAc)2]/PPh3 [J].
Butler, DCD ;
Inman, GA ;
Alper, H .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5887-5890
[6]   A novel entry toward 2-imino-1,3-thiazolidines and 2-imino-1,3-thiazolines by ring transformation of 2-(thiocyanomethyl)aziridines [J].
D'hooghe, M ;
Waterinckx, A ;
De Kimpe, N .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :227-232
[7]   CONFORMATIONAL AND SPECTRAL INVESTIGATIONS OF THIAZOLIDINONE DERIVATIVES BY H-1 AND C-13 NMR-SPECTROSCOPY [J].
DOGAN, I ;
ICLI, S .
SPECTROSCOPY LETTERS, 1983, 16 (07) :499-511
[8]   Electrocatalytic Aldol Addition of Cyclic 1,3-Ketoesters to Isatins: Acetone as a Solvent for the Efficient and Facile Electrochemically Induced Way to 3-Substituted-3-Hydroxyindol-2-One Scaffold [J].
Elinson, M. N. ;
Merkulova, V. M. ;
Ilovaisky, A. I. ;
Chizhov, A. O. ;
Barba, F. ;
Batanero, B. .
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2012, 159 (11) :G123-G127
[9]  
Elinson M. N., 2018, ELECTROCATALYSIS, V9
[10]   Electrocatalytic tandem Knoevenagel-Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold [J].
Elinson, Michail N. ;
Merkulova, Valentina M. ;
Ilovaisky, Alexey I. ;
Barba, Fructuoso ;
Batanero, Belen .
ELECTROCHIMICA ACTA, 2011, 56 (24) :8219-8223