Iron Mediated Desulfurization and C-N Bond Formation: Strategy for the Synthesis of Thioureas

被引:2
作者
Pendem, Venkata Bhavanarushi [1 ]
Nannapaneni, Madhavi [1 ]
机构
[1] JKC Coll, PG Dept Chem, Guntur 522006, Andhra Pradesh, India
关键词
Anilines; iron catalyst; thiocarbamate; thioureas; C-N bond formation; heterocycle; MICROWAVE-ASSISTED SYNTHESIS; SOLVENT-FREE SYNTHESIS; ONE-POT SYNTHESIS; N; N'-DISUBSTITUTED THIOUREAS; DERIVATIVES; THIOHYDANTOINS;
D O I
10.2174/1570178615666180412110323
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient and simple protocol for the construction of aromatic and aliphatic thioureas from their respective amines in the presence of cheap, readily available and air-stable iron catalyst in one pot three steps reaction is described. All the reactions were carried out under optimized reaction conditions to get the target products in good to excellent yields and shorter reaction time.
引用
收藏
页码:1025 / 1029
页数:5
相关论文
共 28 条
[1]   A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: A strategy for diversity amplification [J].
Batey, RA ;
Powell, DA .
ORGANIC LETTERS, 2000, 2 (20) :3237-3240
[2]   THE CHEMOTHERAPY OF EXPERIMENTAL TUBERCULOSIS .3. THE SYNTHESIS OF THIOSEMICARBAZONES AND RELATED COMPOUNDS [J].
BERNSTEIN, J ;
YALE, HL ;
LOSEE, K ;
HOLSING, M ;
MARTINS, J ;
LOTT, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (03) :906-912
[3]   Condensation of thiourea derivatives with carbonyl compounds:: one-pot synthesis of N-alkyl-1,3-thiazol-2-amines and of 3-alkyl-1,3-thiazolimines [J].
Boga, C ;
Forlani, L ;
Silvestroni, C ;
Corradi, AB ;
Sgarabotto, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10) :1363-1368
[4]   Electrochemical and peroxidase oxidation study of N′-hydroxyguanidine derivatives as NO donors [J].
Cai, TW ;
Xian, M ;
Wang, PG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (11) :1507-1510
[5]   Reductive alkylation of thioureas:: a highly practical synthesis of unsymmetrical N,N′-disubstituted thioureas [J].
Ciszewski, L ;
Xu, DQ ;
Repic, J ;
Blacklock, TJ .
TETRAHEDRON LETTERS, 2004, 45 (43) :8091-8093
[6]   Microwave assisted synthesis of fluorinated hexahydro 1,3,5-triazine derivatives in aqueous medium and one pot synthesis of 1,2,4-triazolo(4,3-a)1,3,5-triazines [J].
Dandia, A ;
Arya, K ;
Sati, M .
SYNTHETIC COMMUNICATIONS, 2004, 34 (06) :1141-1155
[7]   REACTIONS OF LONG-CHAIN AMINES .6. PREPARATION OF THIOUREAS [J].
ERICKSON, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :483-484
[8]  
Frank R.L., 1955, ORG SYNTH, V3, P735
[9]   A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCI/NaOH [J].
Heinelt, U ;
Schultheis, D ;
Jäger, S ;
Lindenmaier, M ;
Pollex, A ;
Beckmann, HSG .
TETRAHEDRON, 2004, 60 (44) :9883-9888
[10]   Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N′-(3-substituted phenyl)-N′-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers [J].
Hu, LY ;
Guo, JQ ;
Magar, SS ;
Fischer, JB ;
Burke-Howie, KJ ;
Durant, GJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) :4281-4289