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

页码：1341 / 1348

页数：8

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
Agarwal, A
Rani, S
Vankar, YD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) : 6137 - 6140
[2] FLUORIDE-ALUMINA REAGENTS - THE ACTIVE BASIC SPECIES
ANDO, T
CLARK, JH
CORK, DG
HANAFUSA, T
ICHIHARA, J
KIMURA, T
[J]. 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
ANDO, T
BROWN, SJ
CLARK, JH
CORK, DG
HANAFUSA, T
ICHIHARA, J
MILLER, JM
ROBERTSON, MS
[J]. 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
Bertaina-Anglade, Valerie
La Rochelle, Christophe Drieu
Scheller, Dieter K. A.
[J]. 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
Bezbaruah, Pranjal
Gogoi, Junali
Rao, Kommuri S.
Gogoi, Pranjal
Boruah, Romesh C.
[J]. TETRAHEDRON LETTERS, 2012, 53 (33) : 4389 - 4392
[9] KF/Al2O3 mediated organic synthesis
Blass, BE
[J]. 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
Blass, BE
Harris, CL
Portlock, DE
[J]. TETRAHEDRON LETTERS, 2001, 42 (09) : 1611 - 1613

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