Synthesis of 2,3-disubstituted thiophenes from ketoalkynes

Download

index.pdf

Date

2013

Author

Vatansever, Erol Can

Metadata

Show full item record

Item Usage Stats

293
views

95
downloads

Synthesis of thiophene containing compounds are of particular interest in synthetic organic chemistry. Besides the importance for synthetic organic chemistry, thiophene derivatives are used in applied research such as drug synthesis and study of functional materials. In this thesis, a new methodology for developing of 2,3-disubstituted thiophenes was developed. This methodology utilizes readily available compounds in a two-step synthesis to provide a facile access to the 2,3-disubstituted thiophenes. In the first step, ketoalkynes were prepared by Sonogashira coupling of readily available acyl chlorides and terminal alkynes. Then they were reacted with 2,5-dihydroxy-1,4-dithiane in the presence of triethylamine to yield alcohol intermediates. Finally, alcohol intermediates were dehydrated by treatment with silica gel to yield 2,3-disubstituted thiophenes.

Subject Keywords

Thiophenes., Ketones., Ketoalkynes., Alicyclic compounds., Organic cyclic compounds.

URI

http://etd.lib.metu.edu.tr/upload/12616671/index.pdf
https://hdl.handle.net/11511/23154

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis and characterization of conducting copolymers of thiophene-3-yl acetic acid cholesteryl ester with pyrrole Çırpan, Ali; Toppare, Levent Kamil; YAGCI, Y (2002-05-01) A new polythiophene containing a cholesteryl side chain in the beta-position was chemically polymerised in nitromethane/carbontetrachloride using FeCl3 as the oxidizing agent. Polymerisation was also achieved by constant current electrolysis in dichloromethane. Subsequently, conducting copolymers of thiophene-3-yl acetic acid cholesteryl ester (CM), PCM1 (obtained from chemical polymerisation method) and PCM4 (obtained from constant current electrolysis) with pyrrole were synthesized using p-toluene sulfoni...
Synthesis of New Squaramide Based Organocatalyst and Its Application for Enantioselective Synthesis of Organic Compounds Özdemir, Özge; Doğan, Özdemir; Department of Chemistry (2022-9-19) Organocatalytic asymmetric synthesis of organic compounds is one of the important fields of synthetic organic chemistry. Organocatalysts are small chiral organic molecules having certain functional groups, such as hydroxy, amino, amido etc. These catalysts are environmentally more friendly than the alternative chiral metal catalysts. Therefore, they are more popular and studied more than the metal catalysts. On the other hand, there are no organocatalysts that work well for every organic reaction. Here in t...
The Synthesis of 6- and 7- membered heterocyclic ring systems fused to pyridine ring Dinçoflaz, Yasemin; Balcı, Metin; Department of Chemistry (2013) The synthesis of the nitrogen containing heterocyclic compounds is one of the leading research areas throughout the organic chemistry due to their significant activities in biological systems. Among the various biologically active molecules, pyridine-fused ring systems are of prime importance on the grounds of their proven clinical roles. The coupling reactions with 6-membered heterocyclic compounds and diazepines gave rise to new pharmalogical compounds in recent years. Therefore, our object was the synthe...
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005) A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
SYNTHESİS OF NEW PHOSPHONİC ACİD DRİVATİVES AND THEIR USE AS AN ORGANOCATALYSTS FOR ENANTİOSELECTİVE SYNTHESIS OF ORGANIC COMPOUNDS Doğan, Özdemir(2017-12-31) SYNTHESİS OF NEW PHOSPHONİC ACİD DRİVATİVES AND THEIR USE AS AN ORGANOCATALYSTS FOR ENANTİOSELECTİVE SYNTHESIS OF ORGANIC COMPOUNDS

Citation Formats

E. C. Vatansever, “Synthesis of 2,3-disubstituted thiophenes from ketoalkynes,” M.S. - Master of Science, Middle East Technical University, 2013.