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


Thesis Type: Postgraduate

Institution Of The Thesis: Middle East Technical University, Faculty of Arts and Sciences, Department of Chemistry, Turkey

Approval Date: 2006

Thesis Language: English

Student: Fadile Kapaklı

Supervisor: CİHANGİR TANYELİ

Abstract:

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.