An efficient one-pot synthesis of N-(substituted phenyl)-1,2,5-thiadiazolidine-2-carboxamide 1,1-dioxide derivatives

被引:3
作者
Hessainia, Sihem [1 ]
Boukhari, Abbes [1 ]
Cheraiet, Zinelaabidine [2 ]
机构
[1] Badji Mokhtar Annaba Univ, Dept Chem, Lab Organ Synth Modeling & Optimizat Chem Proc, POB 12, Annaba 23000, Algeria
[2] Ecole Super Technol Ind, Cite Saf Saf BP 21823000, Annaba, Algeria
关键词
BIOLOGICAL EVALUATION; ANTITUMOR EVALUATION; INHIBITORS; SULFONYLUREAS;
D O I
10.1002/jhet.3767
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2,5-Thiadiazolidine-1,1-dioxide carboxamide derivatives 3a-3n are novel heterocyclic compounds synthesized by multicomponent condensation reaction in one pot of aniline, chlorosulfonyl isocyanate, and 2-chloroethylamine hydrochloride which is used as a useful precursor under mild conditions. This reaction is realized with high atom economy, at room temperature and in a short reaction time. Series of these desired products are obtained from good to excellent yields within 2 hours in all cases. All the synthesized compounds are characterized by H-1, C-13 NMR, MS, and HMBC/HSQC spectroscopy.
引用
收藏
页码:218 / 224
页数:7
相关论文
共 27 条
[1]   Synthesis of 5-Aryl-3-(methylsulfanyl)-1H-pyrazoles via Three-Component Reaction of 1,1-Bis(methylsulfanyl)-2-nitroethene, Aromatic Aldehydes, and Hydrazine [J].
Alizadeh, Abdolali ;
Zand, Hamid Reza Esmaili ;
Saberi, Vahid ;
Mokhtari, Javad .
HELVETICA CHIMICA ACTA, 2013, 96 (12) :2240-2244
[2]   Synthesis, characterization and in vitro biological evaluation of some novel diarylsulfonylureas as potential cytotoxic and antimicrobial agents [J].
Avupati, Vasudeva Rao ;
Yejella, Rajendra Prasad ;
Guntuku, Girijasankar ;
Gunta, Pradeepsagar .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) :1031-1035
[3]   Synthesis of a small library of non-symmetric cyclic sulfamide HIV-1 protease inhibitors [J].
Ax, Anna ;
Joshi, Advait A. ;
Orrling, Kristina M. ;
Vrang, Lotta ;
Samuelsson, Bertil ;
Hallberg, Anders ;
Karlen, Anders ;
Larhed, Mats .
TETRAHEDRON, 2010, 66 (23) :4049-4056
[4]  
Dhar N. D., 1986, SYNTHESIS-STUTTGART, V6, P437
[5]   Cyclosulfamide-based derivatives as inhibitors of noroviruses [J].
Dou, Dengfeng ;
Mandadapu, Sivakoteswara R. ;
Alliston, Kevin R. ;
Kim, Yunjeong ;
Chang, Kyeong-Ok ;
Groutas, William C. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 47 :59-64
[6]   Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction [J].
El-Deeb, Ibrahim M. ;
Bayoumi, Said M. ;
El-Sherbeny, Magda A. ;
Abdel-Aziz, Alaa A. -M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (06) :2516-2530
[7]   Synthesis and antitumor evaluation of novel diarylsulfonylurea derivatives: Molecular modeling applications [J].
El-Sherbeny, Magda A. ;
Abdel-Aziz, Alaa A. -M. ;
Ahmed, Musa A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :689-697
[8]  
Fahmy M. A. H., 1980, Eur. Pat. Appl., Patent No. [1980 , 36, 198036]
[9]   SYNTHESIS AND ANTI-HIV-1 ACTIVITY OF NEW THIADIAZEPINDIOXIDES [J].
GIANNOTTI, D ;
VITI, G ;
NANNICINI, R ;
PESTELLINI, V ;
BELLAROSA, D .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (14) :1461-1466
[10]   NEW DIBENZOTHIADIAZEPINE DERIVATIVES WITH ANTIDEPRESSANT ACTIVITIES [J].
GIANNOTTI, D ;
VITI, G ;
SBRACI, P ;
PESTELLINI, V ;
VOLTERRA, G ;
BORSINI, F ;
LECCI, A ;
MELI, A ;
DAPPORTO, P ;
PAOLI, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (04) :1356-1362