Reaction of propargyl aldehydes with hydrazinium salts: synthesis of ferrocenyl and Phenyl substituted pyrazoles

Download

index.pdf

Date

2008

Author

Pınar, Ayşe Nur

Metadata

Show full item record

Item Usage Stats

319
views

127
downloads

Pyrazoles have been focus of a large number of investigations in the design and synthesis of novel biologically active agents that show remarkable medicinal activities. Although pyrazoles have been studied for over a century as an important class of heterocyclic compounds, they still continue to attract considerable attention due to the wide range of medicinal activities they possess. Recent studies have shown that combination of a ferrocenyl unit with structural features of pyrazoles can lead to products with enhanced or/and unexpected biological activity since several ferrocene derivatives have already been shown to be active against a number of tumors. As a result, we have investigated the reaction of 3-ferrocenylpropynal with hydrazinium salts. As anticipated, these reactions afforded two kinds of pyrazoles, namely 1-alkyl/aryl-5-ferrocenylpyrazoles (1,5-isomer) and 1-alkyl/aryl-3- ferrocenylpyrazoles (1,3-isomer). In most cases, 1,5-pyrazole isomers have resulted from these reactions as the single or the major product of the reactions. The structures of 1-benzyl-5-ferrocenylpyrazole, 1-phenyl-5-ferrocenyl-pyrazole and 1- (2-hydroxy-ethyl)-3-ferrocenylpyrazole were identified by X-ray single crystal analysis. The analogous reactions between 3-phenylpropynal and hydrazinium salts were also studied, which afforded 1-alkyl/aryl-5-phenylpyrazoles (1,5-isomer) and/or v 1-alkyl/aryl-3-phenylpyrazoles (1,3-isomer). The regioselectivity of the reactions is mainly governed by the nature of the substituents in hydrazine derivative.

Subject Keywords

Chemistry., Chemistry, Organic

URI

http://etd.lib.metu.edu.tr/upload/3/12609769/index.pdf
https://hdl.handle.net/11511/17726

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles by electrophilic cyclization Karahan Dağ, Fulya; Zora, Metin; Department of Chemistry (2011) Pyrazoles have been intensely studied in the design and synthesis of biologically active agents because they display considerable medicinal activities. Recent studies have shown that integration of a ferrocenyl unit with structural features of pyrazoles can result in the formation of the new products with enhanced or/and unexpected biological activity since several ferrocene derivatives have already been illustrated to be active against a number of tumors. Therefore, we have investigated the electrophilic c...
Addition of carbonyl compounds to the cyclic olefins : synthesis of cyclitols Altun, Yasemin; Balcı, Metin; Department of Chemistry (2008) Cyclitols have attracted a great deal of attention in recent years owing to biological activities exhibited by them and also their usefulness in the synthesis of other natural products and pharmaceuticals. Carbasugars are also a derivative of cyclitols and they are cyclic monosaccharide analogues which posses CH2OH group in their structure. In this study, novel synthetic strategies leading to cyclitol derivatives were investigated and the synthesis of tetraol (72) and pentaol (73) derivatives containing CH2...
The development of the novel synthesis for conduritols Cantekin, Seda; Balcı, Metin; Department of Chemistry (2006) Conduritols have attracted a great deal of attention in recent years owing to biological activities exhibited by them and also their usefulness in the synthesis of other natural products and pharmaceuticals. Conduritols show interesting inhibitor activity for some glycosidases and serve as important intermediates in the synthesis of inositols. In this study, novel synthetic strategies leading to highly functionalized cyclohexene derivative containing an aromatic ring, namely phenyl-substituted conduritol wa...
Synthesis of ferrocenyl cycloheptadienones Açıkgöz, Canet; Zora, Metin; Department of Chemistry (2005) Synthesis of seven-membered ring systems such as cycloheptadienones has attracted a great deal of attention in organic chemistry since they are present in a variety of biologically important molecules. Incorporation of the essential structures of such compounds with a ferrocene moiety instead of an aryl group could provide subtances with enhanced antitumor activities since some ferrocene derivatives have already proved to be active against a number of tumors. To develop a ferrocenyl-substituted seven-member...
Studies on the reaction of acyl phosphonates with aldehydes in the presence of proline Yalçınkaya, Hatice; Demir, Ayhan Sıtkı; Department of Chemistry (2009) Acyl phosphonates are interesting precursors for the synthesis of biologically active compounds. In the first part, the acyl phosphonates are synthesized starting from the corresponding acyl chloride. The acyl chlorides are converted into acyl phosphonates by using trialkylphosphites. The reaction of acyl phosphonates with aldehydes in the presence of proline furnished not the suggested aldol products via proline catalyzed aldol reaction but bicyclic products via one pot tricomponent 1,3-dipolar cycloadditi...

Citation Formats

A. N. Pınar, “Reaction of propargyl aldehydes with hydrazinium salts: synthesis of ferrocenyl and Phenyl substituted pyrazoles,” M.S. - Master of Science, Middle East Technical University, 2008.