New strategy for the synthesis of chiral N-substituted-3,4-dialkoxypyrrole from 2,5-dihydro-2,5-dimethoxyfuran

Download

index.pdf

Date

2006

Author

Kapaklı, Fadile

Metadata

Show full item record

Item Usage Stats

283
views

81
downloads

Pyrroles are very valuable class of substances which have wide usage area in organic synthesis. In this study, chiral 3,4-dialkoxy-N-substituted pyrrole derivatives were synthesized. These compounds are widely used as building blocks for the synthesis of natural compounds that have focused on heterocyclic rings in their structures. In addition, chiral pyrrole derivatives can be used as monomers for the synthesis of chiral conducting polymers which have received great interest due to their potential applications as electrodes for electrochemical asymmetric synthesis, stereoselecive analyses and in many areas, such as electronics, electrochromic devices, polymeric batteries, antielectronic coatings and functional membranes. 3,4-dialkoxy-N-substituted chiral pyrrole derivatives were synthesized starting from 2,5-dimethoxy-2,5-dihydrofuran which is a commercially available, inexpensive material. After oxidation, the resultant diol were protected with alkoxy goups and then correponding 3,4-dialkoxy-N-substituted chiral pyrrole derivatives were afforded via pyrrolization reaction by using several chiral amines or aminoalcohols.

Subject Keywords

Chemistry, Organic

URI

http://etd.lib.metu.edu.tr/upload/3/12607334/index.pdf
https://hdl.handle.net/11511/16268

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis of novel chiral N,N-dialkyl substituted 1,4-amino alcohols and applications in asymmetric transformation reactions Çakır, Esen; Tanyeli, Cihangir; Department of Chemistry (2007) Amino alcohols are valuable bioactive substances and frequently used as chiral catalyst in various asymmetric transformation reactions. In the synthetic route, the asymmetric synthesis of novel chiral N,N-dialkyl substituted chiral 1,4-amino alcohols are performed starting with meso-anhydride 38. Quinine-mediated desymmetrization of the anhydride with methanol afforded (2S,3R)-cis-monoester 39 with a high enantiomeric excess (up to 98% ee). Chemoselective amidation of hemiester with various N,N-dialkyl subs...
Oxidative ring opening reactions of a-hydroxy ketones Aybey, Ayşe; Demir, Ayhan Sıtkı; Department of Chemistry (2008) Chiral polyfunctionalized 1,5-dicarbonyl compounds are important synthetic intermediates and starting materials for many biologically active compounds so their synthesis has a great importance in the literature. In the first step, 1,3-cyclohexandione and other b-diketone derivatives are protected under acid catalyzation and their corresponding b-keto enol ether derivatives are obtained. These b-keto enol ethers are then converted to a-acetoxy enones in racemic form by Mn(OAc)3 mediated oxidation. Enzymatic ...
AN EFFICIENT SYNTHESIS OF SUBSTITUTED 2H-PYRAN-2-ONE DERIVATIVES VIA THE CONJUGATED ADDITION OF THE ENOLATES OF CARBONYL-COMPOUNDS TO ENAMINOESTERS DEMIR, AS; Tanyeli, Cihangir; URKMEZKARAASLAN, R; SAYRAC, T (Informa UK Limited, 1991-01-01) Short simple synthesis of alkenoic acid esters and their intramolecular cyclization products, 2H-Pyran-2-ones from enolates of carbonyl compounds and enaminoesters are described.
Synthesis of various camphor-based chiral pyridine derivatives Işık, Murat; Tanyeli, Cihangir; Department of Chemistry (2005) Chiral aromatic nitrogen heterocycles are finding many applications in asymmetric organic synthesis, particularly as ligands in the preparation of chiral metal complexes. Since camphor-based chiral auxiliaries are known to be especially effective, a number of pyridines fused to the camphor skeleton have been reported. It is well known that nicotinic acid and its derivatives exhibiting qualitatively the biological activity of nicotinamide, which acts as an electron acceptor in many biological redox reactions...
Development of new synthetic methodologies for the synthesis of unusual isocoumarin and indole derivatives:The chemistry of homophthalic acid Özcan, Sevil; Balcı, Metin; Department of Chemistry (2007) Many heterocyclic compounds containing nitrogen, oxygen and sulfur show wide range of physiological activities and their synthesis has always been attracted the interest of chemists. The aim of this research is to develop new synthetic methodologies leading to the synthesis of new derivatives of isocoumarines, indoles, isoquinolines, benzodiazepinones and quinazolines, which have been found to show important biological activities. Starting from homophthalic acid and bishomophthalic acid the corresponding ac...

Citation Formats

F. Kapaklı, “New strategy for the synthesis of chiral N-substituted-3,4-dialkoxypyrrole from 2,5-dihydro-2,5-dimethoxyfuran,” M.S. - Master of Science, Middle East Technical University, 2006.