KF/Al2O3/PEG-400: An Efficient Catalytic System for the Fiesselmann-Type Synthesis of Thiophene Derivatives

被引:14
作者
Bezboruah, Pranjal [1 ]
Gogoi, Pranjal [1 ]
Gogoi, Junali [1 ]
Boruah, Romesh C. [1 ]
机构
[1] CSIR North East Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 10期
关键词
Fiesselmann synthesis; KF/Al2O3/PEG-400; thiophene; unsaturated aldehyde; unsaturated nitrile; BIOLOGICAL EVALUATION; FLUORIDE; AGENT;
D O I
10.1055/s-0033-1338299
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and mild protocol has been developed for the synthesis of novel steroidal and nonsteroidal thiophene derivatives from beta-halo-alpha,beta-unsaturated aldehydes using KF/Al2O3/PEG-400 as an efficient catalytic system. The beta-halo-alpha,beta-unsaturated aldehydes are synthesized from the corresponding ketones using Vilsmeier formylation reaction and converted into beta-halo-alpha, beta-unsaturated nitriles. The synthetic protocol is subsequently applied to the synthesis of 3-aminothiophene derivatives using beta-halo-alpha, beta-unsaturated nitriles.
引用
收藏
页码:1341 / 1348
页数:8
相关论文
共 48 条
[1]   Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals [J].
Agarwal, A ;
Rani, S ;
Vankar, YD .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :6137-6140
[2]   FLUORIDE-ALUMINA REAGENTS - THE ACTIVE BASIC SPECIES [J].
ANDO, T ;
CLARK, JH ;
CORK, DG ;
HANAFUSA, T ;
ICHIHARA, J ;
KIMURA, T .
TETRAHEDRON LETTERS, 1987, 28 (13) :1421-1424
[3]   ALUMINA-SUPPORTED FLUORIDE REAGENTS FOR ORGANIC-SYNTHESIS - OPTIMIZATION OF REAGENT PREPARATION AND ELUCIDATION OF THE ACTIVE SPECIES [J].
ANDO, T ;
BROWN, SJ ;
CLARK, JH ;
CORK, DG ;
HANAFUSA, T ;
ICHIHARA, J ;
MILLER, JM ;
ROBERTSON, MS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (08) :1133-1139
[4]  
[Anonymous], 2003, GREE CHEM
[5]  
[Anonymous], HDB ORGANIC CONDUCTI
[6]  
[Anonymous], 1998, Electronic materials: the oligomer approach
[7]   Antidepressant properties of rotigotine in experimental models of depression [J].
Bertaina-Anglade, Valerie ;
La Rochelle, Christophe Drieu ;
Scheller, Dieter K. A. .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2006, 548 (1-3) :106-114
[8]   Microwave-assisted novel and efficient one-pot synthesis of fused steroidal and non-steroidal isothiazoles [J].
Bezbaruah, Pranjal ;
Gogoi, Junali ;
Rao, Kommuri S. ;
Gogoi, Pranjal ;
Boruah, Romesh C. .
TETRAHEDRON LETTERS, 2012, 53 (33) :4389-4392
[9]   KF/Al2O3 mediated organic synthesis [J].
Blass, BE .
TETRAHEDRON, 2002, 58 (46) :9301-9320
[10]   A facile, selective KF/Al2O3 mediated method for the deprotection of aryl silyl ethers and preparation of aryl SEM ethers [J].
Blass, BE ;
Harris, CL ;
Portlock, DE .
TETRAHEDRON LETTERS, 2001, 42 (09) :1611-1613