Synthesis of new pyrrole derivatives from npropargylic β-enaminones

Date

2020

Author

Kanova, Nilay

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

267
views

0
downloads

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 of heterocyclic compounds, especially pyrroles. In this study, we have investigated the synthesis of new 2-acetylpyrrole derivatives which may have potential biological activities. Various pyrrole derivatives have been synthesized with two unprecedented way which are synthesis method from 1,4- oxazepines and one-pot two-step synthesis method from N-propargylic βenaminones. Firstly, α,β-alkynic ketone derivatives have been synthesized via Sonogashira coupling reaction between benzoyl chlorides and terminal alkynes. After synthesizing α,β-alkynic ketone derivatives, N-propargylic β-enaminone derivatives vi have been synthesized by the conjugate addition between propargylamine and the corresponding α,β-alkynic ketones. Secondly, the cyclization of N-propargylic β-enaminones have been carried out for the synthesis of 2-methylene-2,3-dihydro-1,4-oxazepines. A number of 2- methylene-2,3-dihydro-1,4-oxazepine derivatives have been synthesized in the presence of ZnCl2. Lastly, we have investigated the synthesis of 2-acetylpyrroles by using 1,4- oxazepines and N-propargylic β-enaminones as starting materials. We have achieved that the synthesis of the mentioned pyrroles via two original synthesis procedures. In the light of these two methods, 19 novel pyrrole derivatives have been synthesized.

Subject Keywords

Heterocyclic compounds., Keywords: Heterocyclic compounds, N-propargylic β-enaminones, pyrroles, 1,4- oxazepines.

URI

http://etd.lib.metu.edu.tr/upload/12625538/index.pdf
https://hdl.handle.net/11511/45784

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Facile synthesis of (4-nitrophenyl)thio-substituted 1- pyrrolines Korkmaz, Esra; Zora, Metin; Department of Chemistry (2019) The importance of heterocyclic compounds is enormous in synthetic organic chemistry due to their presence in bioactive molecules. Five-membered 1-pyrrolines are one of the most important classes of them. They have recently drawn great attention from synthetic chemists since they have a prominent role for the synthesis of a great number of pharmaceutical molecules. Therefore, there is intense research on their synthesis. In this project, we concentrated on the synthesis of (4-nitrophenyl)thio-substituted 1- ...
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...
Development of new methods for the synthesis of five-, six-and seven-membered heterocyclic compounds Karadeniz, Eda; Zora, Metin; Department of Chemistry (2019) Synthesis of heterocyclic compounds has become an important area among organic chemists since they occupy a unique position in the design and synthesis of novel biologically active agents that exhibit noteworthy medicinal activities. In this regard, N-propargylic β-enaminones have been recognized as valuable substrates in synthesis because they afford a variety of heterocyclic compounds upon treatment with proper reagents. In this study, new reactivity patterns of N-propargylic β-enaminones were investigate...
Synthesis of 2,3-disubstituted thiophenes from ketoalkynes Vatansever, Erol Can; Balcı, Metin; Department of Chemistry (2013) 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...
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...

Citation Formats

N. Kanova, “Synthesis of new pyrrole derivatives from npropargylic β-enaminones,” Thesis (M.S.) -- Graduate School of Natural and Applied Sciences. Chemistry., Middle East Technical University, 2020.