Unexpected cyclization of dipyrilydl-glycoluril in the presence of formaldehyde and strong acid : a new scaffold with a potential as a receptor and synthesis of vairous calixarene precursors

Download

index.pdf

Date

2005

Author

Cevheroğlu, Orkun

Metadata

Show full item record

Item Usage Stats

130
views

60
downloads

This thesis covers combination of two independent works accomplished throughout the study. One part research is about the unexpected cyclization of Dipyridyl-glycoluril, and the other part is about synthesis of precursor calix[4]arene derivatives. In an attempted synthesis of peripherally pyridine substituted cucurbituril, an unexpected cyclized product was obtained. A careful NMR analysis followed by mass spectrometry and preliminary crystallographic analyses, helped us in resolving the structure. The structure has two quaternized pyridine functionalities and a groove suitable as a potential receptor site. In addition, just like the parent glycoluril structure, two remaining urea-derived nitrogens can be alkylated by alkyl halides. Thus, we believe this high yielding reaction may become an entry point to a new class of anion receptors. In the second work, certain important calix[4]arene derivatives were synthesized. They are the building blocks of important potential molecular, anion and cation sensing, and enzyme mimics. For these precursor molecules, functionalizations both on lower and upper rim have been studied. A careful study on NMR data has been performed and detailed investigation on the NMR data was discussed herein. Applying further one or two step procedures produces important target molecules having potential as sensors or artificial enzymes.

Subject Keywords

Chemistry, Organic

URI

http://etd.lib.metu.edu.tr/upload/12606423/index.pdf
https://hdl.handle.net/11511/15342

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis and reactions of alpha-keto-beta-hydroxyphosphonates Barış, Şehriban; Demir, Ayhan Sıtkı; Department of Chemistry (2007) This thesis presents synthesis and different reactions of alpha-keto-beta-hydroxyphosphonates. Toward this aim, the hydroxyl functionality of alpha-hydroxycarboxylic acids were protected with alkyl or acyl groups and then formation of acid chloride followed by the reaction with trialkylphosphite furnished protected alpha-keto-beta-hydroxyphosponates. Nucleophilic addition reactions were applied to these compounds to obtain quaternary alcohols with phosphonate functionality. The addition reactions were tried...
Xanthene-based artifical enzymes and a dimeric calixpyrrole as a chromogenic chemosensor Şaki, Neslihan; Akkaya, Engin Umut; Department of Biochemistry (2004) This thesis covers the combination of two seperate work accomplished during the throughout the study. In the first part of the study, xanthene based artificial enzymes were synthesized, and kinetic hydrolysis studies done. Artificial enzyme design is an active field of supramolecular chemistry and metalloenzymes are attractive targets in such studies. Enzymatic catalysis is essentially a ءmultifuctional̕ catalysis. As part of our work, we designed and synthesized three novel xanthene derivatives. All three ...
Synthesis of heteroaryl substituted dihydrofuran and dihydropyran derivatives by green chemistry approach Demirci, Sema; Tanyeli, Cihangir; Department of Chemistry (2009) The thesis subject is mainly involved in Green Chemistry approach. Thiophene, furan and pyridine carboxaldehydes were chosen as starting compounds and vinylation and allylation with Grignard reaction afforded the corresponding racemic heteroaryl substituted allylic and homoallylic alcohols. Subsequent resolution with enzymes (PS-Amano II, Lipozym and Novazym 435) gave enantiomerically enriched alcohols with the e.e. values varied between 65 and 99%. The absolute configurations of all substrates are known. A...
Synthesis of linkers and mediators for electrochemical reactor design and enantiopure synthon preparation Akbaşoğlu, Naime; Demir, Ayhan Sıtkı; Department of Chemistry (2009) The thesis subject is mainly involved in Green Chemistry approach. Thiophene, furan and pyridine carboxaldehydes were chosen as starting compounds and vinylation and allylation with Grignard reaction afforded the corresponding racemic heteroaryl substituted allylic and homoallylic alcohols. Subsequent resolution with enzymes (PS-Amano II, Lipozym and Novazym 435) gave enantiomerically enriched alcohols with the e.e. values varied between 65 and 99%. The absolute configurations of all substrates are known. A...
Development of acyl anion precursors and their applications Reis, Ömer; Demir, Ayhan Sıtkı; Department of Chemistry (2005) This thesis presents the development of new acyl anion precursors and their applications. The main concern of this thesis was to make use of acyl anion precursors in catalytic bond forming reactions. Toward this aim, previously known cyanide ion catalyzed cleavage of benzils was investigated in scope and efficiency in unsymmetrical benzoin condensation. Although benzils were proved to be useful entities as acyl anion precursors in benzoin condensation, they suffer some major drawbacks. Therefore acylphospho...

Citation Formats

O. Cevheroğlu, “Unexpected cyclization of dipyrilydl-glycoluril in the presence of formaldehyde and strong acid : a new scaffold with a potential as a receptor and synthesis of vairous calixarene precursors,” M.S. - Master of Science, Middle East Technical University, 2005.