Unexpected synthesis of novel O-ethyl-P-aryl-N-(thiophen-2-yl) phosphonamidothioates from ethyl 2-aminothiophene-3-carboxylates and Lawesson's reagent

被引:3
作者
Khalladi, Khaoula [1 ]
Touil, Soufiane [1 ]
机构
[1] Univ Carthage, Fac Sci Bizerta, Dept Chem, Lab Heteroatom Organ Chem, Jarzouna 7021, Tunisia
关键词
thiophenes; Lawesson's reagent; thiophosphonamides; phosphonamidothioates; carbonyl sulfide extrusion; ORGANOPHOSPHORUS COMPOUNDS; BIOLOGICAL EVALUATION; DERIVATIVES; THIOPHENE; ANALOGS;
D O I
10.1080/17415993.2013.815750
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of ethyl 2-aminothiophene-3-carboxylates with a stoichiometric amount of Lawesson's reagent (LR) gave novel O-ethyl-P-aryl-N-(thiophen-2-yl) phosphonamidothioate derivatives rather than the expected thienothiazaphosphorines. A possible reaction mechanism, involving a carbonyl sulfide extrusion, is proposed. [GRAPHICS] .
引用
收藏
页码:145 / 151
页数:7
相关论文
共 20 条
[1]   Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety [J].
Bondock, Samir ;
Fadaly, Walid ;
Metwally, Mohamed A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :3692-3701
[2]   New thiophene analogues of kenpaullone:: synthesis and biological evaluation in breast cancer cells [J].
Brault, L ;
Migianu, E ;
Néguesque, A ;
Battaglia, E ;
Bagrel, D ;
Kirsch, G .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (08) :757-763
[3]   STUDIES ON ORGANO-PHOSPHORUS COMPOUNDS .36. SIMPLE NEW ROUTES TO PHOSPHORINS FROM 2-HYDROXYBENZOIC, 2-MERCAPTOBENZOIC AND 2-AMINOBENZOIC ACIDS AND THEIR DERIVATIVES [J].
ELBARBARY, AA ;
LAWESSON, SO .
TETRAHEDRON, 1981, 37 (15) :2641-2646
[4]   Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents [J].
Fakhr, Issa M. I. ;
Radwan, Mohamed A. A. ;
El-Batran, Seham ;
El-Salam, Omar M. E. Abd ;
El-Shenawy, Siham M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (04) :1718-1725
[5]   2-AMINO-THIOPHENE AUS METHYLENAKTIVEN NITRILEN CARBONYLVERBINDUNGEN UND SCHWEFEL [J].
GEWALD, K ;
SCHINKE, E ;
BOTTCHER, H .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (01) :94-&
[6]  
GOLOVKO TV, 1995, MENDELEEV COMMUN, P191
[7]   Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives [J].
Isloor, Arun M. ;
Kalluraya, Balakrishna ;
Pai, K. Sridhar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :825-830
[8]   Gas extrusion in natural products total synthesis [J].
Jiang, Xuefeng ;
Shi, Lei ;
Liu, Hui ;
Khan, Akbar H. ;
Chen, Jason S. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (42) :8383-8392
[9]   Synthesis of novel fused thienodiazaphosphorine derivatives from 2-amino-3-cyanothiophenes and Lawesson's reagent [J].
Khalladi, Khaoula ;
Touil, Soufiane .
JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (01) :27-32
[10]   Synthesis and biological evaluation of thiophene [3,2-b] pyrrole derivatives as potential anti-inflammatory agents [J].
Kumar, PR ;
Raju, S ;
Goud, PS ;
Sailaja, M ;
Sarma, MR ;
Reddy, GO ;
Kumar, MP ;
Reddy, VVRMK ;
Suresh, T ;
Hegde, P .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (05) :1221-1230