Synthesis of indole-fused new heterocycles via alkyne cyclizations

Download
2015
Şeybek, Ali Fatih
It is known that many natural and synthetic structures including indole ring have important biological activities. In this thesis, synthesis of pyridine, pyrazine and pyrazinone rings condensed to indole was carried out via alkyne cyclization reactions. In the first part, oxindole was synthesized by reduction of isatin. Then, aldehyde group and chlorine atom was introduced to the C-3 and C-2 positions via Vilsmeier-Haack reaction. After that, Sonagashira coupling reaction led to functionalize C-3 position with an alkyne group. Reaction of the resulting compound with hydrazine gave γ-carboline derivative. In the second part, C-2 and C-3 positions were functionalized by ester and alkyne groups, respectively. We attempted to synthesize diazepinone derivative by using ring closure reaction with hydrazine, but the desired compound could not obtained. In the final part, C-2 position was substituted by an aldehyde group and N-1 position was substituted by a propargyl group starting from indole-2-carboxylic acid. Then, as a result of the reactions of this key compound with variety of amines, indolopyrazine and indolopyrazinone derivatives were synthesized.

Suggestions

Development of a new methodology for the synthesis of haloconduritols and gold catalyzed alkyne cyclizations of n-propargyl substituted indole derivatives /
Kaya, Serdal; Balcı, Metin; Department of Chemistry (2015)
Because of the biological properties and being useful intermediates, haloconduritols became synthetically important molecules. During the last decades, some methodologies have been developed for the construction of haloconduritol derivatives. Our synthetic strategy was based on stereospecific hydroxylation of one of the double bonds of commercially available cyclopentadiene. After protection of the hydroxyl groups as a ketal, the remaining double bond was submitted to the dibromocarbene addition reaction. S...
Synthesis of Functionalized Novel alpha-Amino-beta-alkoxyphosphonates through Regioselective Ring Opening of Aziridine-2-phosphonates
Polat-Cakir, Sidika; Beksultanova, Nurzhan; Doğan, Özdemir (Wiley, 2019-11-01)
Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions p...
Synthesis of indole fused heterocyclic compounds
Kaptı, Tolga; Balcı, Metin; Department of Chemistry (2013)
Nitrogen containing heterocyclic compounds show wide range of biological activities so their syntheses have always been attractive area in organic chemistry. Indole derivatives, which are one of the important example of these biological active compound, are precursors to many pharmaceuticals. The aim of this research is to develop new synthetic methodologies leading to the synthesis of new derivatives of pyrimidoindole and quinoline, which have been found to show important biological activities. In this stu...
SYNTHESIS OF 2,3-DITHIOFENIL DERIVATIVES OF PYRROL ON THE BASIS OF 2,2 '-THIONINE
Maharramov, A. M.; Akay, P.; Akhmedov, I. M.; Safarova, A. S.; Qurbanova, M. M.; Huseynov, E. Z.; Musayeva, S. A. (2019-01-01)
It is known that pyrrole and its derivatives are a part of many important natural compounds. Polymeric semiconductors also were obtained on the basis of 2,5-dithienyl-pyrrole electropolymerization and its derivatives. The work deals with the synthesis of 2,3-dithiophenyl-1H-pyrroles by the reaction of 2,2'-thionine with various enamines.
Synthesis of 2-aziridinyl phosphonates by modified Gabriel-Cromwell reaction and their antibacterial activities
Doğan, Özdemir; Gözen, Ayşe Gül (Elsevier BV, 2011-06-01)
A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.
Citation Formats
A. F. Şeybek, “Synthesis of indole-fused new heterocycles via alkyne cyclizations,” M.S. - Master of Science, Middle East Technical University, 2015.