Synthesis of 2,3-disubstituted thiophenes from ketoalkynes

Vatansever, Erol Can
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.


Mn(OAc)3 promoted addition of an active methylene compound to alkenes: mechanistic studies
Ceyhan, Selin; Balcı, Metin; Department of Chemistry (2015)
Radical cyclization of alkenes is one of the most important methods for the synthesis of cyclic compounds. The one electron oxidant Mn(OAc)3 has been used for many years for the oxidative addition of acetic acid to alkenes to give lactones. In this thesis, various alkenes substituted at 1,2-positions by phenyl and thiophene rings were reacted with active methylene compounds in the presence of Mn(OAc)3∙2H2O. The regioselectivity of the addition were searched. The mechanism for the addition was studied in con...
Synthesis of new pyrrole derivatives from npropargylic β-enaminones
Kanova, Nilay; Zora, Metin; Department of Chemistry (2020)
Heterocyclic compounds are a momentous area of synthetic organic chemistry because of their existence in bioactive molecules. Pyrroles, which are one of the most important classes of heterocyclic compounds, have great importance in pharmaceutical chemistry due to their biological activities. Having these characteristics makes them drawn attention of most chemists to develop new methodologies for the synthesis of pyrroles. Recently, the cyclization of Npropargylic β-enaminones has been used for the synthesis...
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 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...
Synthesis of chiral lactones via the baeyer villiger oxidation of cyclic aromatic acetoxy ketones novel annulation reactions of 2-propynyl-1,3-dicarbonyl compounds to form pyrroles addition of acyl phosphonates to diethyl cyanophosphonate (depc)
Aybey, Asuman; Demir, Ayhan Sıtkı; Department of Chemistry (2009)
Chiral Baeyer-Villiger (BV) oxidation of cyclic ketones allows rapid access to asymmetric lactones as valuable intermediates in organic chemistry and frequently encountered precursors in enantioselective synthesis. In the first part, BV oxidation of functionalized ketones, especially cyclic -hydroxy and acetoxy ketones is described which could be a straightforward route to the -hydroxy lactones and -hydroxyalkanoic acid derivatives. The -acetoxylation of indanone, tetralone and chromanone derivatives by usi...
Citation Formats
E. C. Vatansever, “Synthesis of 2,3-disubstituted thiophenes from ketoalkynes,” M.S. - Master of Science, Middle East Technical University, 2013.