Development of a new method for the synthesis of benzo[h][1,6]naphthyridine derivatives and chromenopyrazinone skeleton

Download
index.pdf
2015
Hoplamaz, Emre
Show full item record
177
views
117
downloads
In the first part of this thesis, a new methodology was developed for the synthesis of benzo[h][1,6]naphthyridine derivatives. Firstly, 2-(diprop-2-ynylamino)benzaldehyde was synthesized starting from 2-aminobenzoic acid in three steps. Then, cyclization reaction was achieved in the presence of propargyl amine and DBU. The expected 3-methylbenzo[h][1,6]naphthyridine was obtained. To generalize this methodology, several derivatives of 2-(diprop-2-ynylamino)benzaldehyde were synthesized by applying Sonogashira coupling reaction in good yields. Cyclization reaction of these derivatives were succeeded by using propargyl amine and DBU. Finally, aryl and methyl substituted benzo[h][1,6]naphthyridine derivatives were obtained in good yields. In the second part, a new synthetic method for the synthesis of a chromenopyrazine and a chromenopyrazinone derivative was developed. Firstly, acetonitrile group was introduced to salicylaldehyde. Then, reaction of this aldehyde with propargyl amine gave imine. DBU-supported cyclization reaction afforded the product, 3-methyl-5H-chromeno[3,4-b]pyrazine. Finally, cyclization product was oxidized with CrO3/pyridine to yield 3-methyl-5H-chromeno[3,4-b]pyrazin-5-one. In order to generalize this reaction, two different aldehyde substituted at the benzene ring were employed. Same procedure for cyclization reaction was applied to get chromenopyrazine derivatives. Unfortunately, expected chromenopyrazine and chromenopyrazinone derivatives were not obtained.
Benzonaphthyridine., Chromenopyrazine., Chromenopyrazinone., Sonogashira coupling.
http://etd.lib.metu.edu.tr/upload/12619120/index.pdf
https://hdl.handle.net/11511/25115
Graduate School of Natural and Applied Sciences, Thesis

Suggestions

Novel annulation reactions for the synthesis of substituted pyrroles darzens reaction of acyl phosphonates with α-bromo ketones : selective synthesis of cis- and transepoxyphosphonates
Emrullah, Mustafa; Demir, Ayhan Sıtkı; Department of Chemistry (2009)
In the first part of this thesis, it is aimed to develope methods for the synthesis of trisubstituted pyrrrole derivatives. 2-Aminopyrrroles, alkoxy and sulfonyl substittitued pyrrole derivatives as well as pirolinones show interesting biological activities and are precursor of well know drugs. Although there is a number of methods for the synthesis of pyrroles, the synthesis of 2-aminopyrroles is limited to few works and is not widely known. Therefore, it is still an important goal in organic chemistry to ...
Synthesis of Novel Benzothiazole-Piperazine Derivatives and Their Biological Evaluation as Acetylcholinesterase Inhibitors and Cytotoxic Agents
GÜRDAL HAKGÖR, ENİSE ECE; Turgutalp, Bengisu; Gulcan, Hayrettin Ozan; Ercetin, Tugba; Şahin, Mustafa; Durmaz, Irem; Atalay, Rengül; Quoc Dat Nguyen, Quoc Dat Nguyen; Sippl, Wolfgang; YARIM YÜKSEL, MİNE (2017-01-01)
Objective and Method: A new series of benzothiazole-piperazine derivatives was synthesized and a complete chemical characterization of the novel compounds was provided. In vitro cytotoxic activities were screened against colorectal (HCT-116), breast (MCF-7) and hepatocellular (Huh7) cancer cell lines by Sulforhodamine B assay.
Design and synthesis of novel substituted indole-acrylamide derivatives and evaluation of their anti-cancer activity as potential tubulin-targeting agents
Hawash, Mohammed; Kahraman, Deniz Cansen; OLĞAÇ, ABDURRAHMAN; Ergun, Sezen Guntekin; Hamel, Ernest; Cetin-Atalay, Rengul; BAYTAŞ, SULTAN (2022-04-01)
Novel compounds containing polar and nonpolar substitutions on the prop-2-en-1-on linker of the trans-indol-3-ylacrylamide scaffold were designed by modeling within the colchicine site of tubulin and then synthesized to determine the role of such substitutions on tubulin polymerization. We first determined the in vitro antiproliferation activities of the compounds against cancer cell lines with a particular focus on hepatocellular carcinoma. The results indicated that five of the compounds showed moderate a...
Development of enhanced ultrafiltration methodologies for the resolution of racemic benzoin
Olceroglu, Ayse Hande; Çalık, Pınar; Yılmaz, Levent (Elsevier BV, 2008-09-15)
In the scope of achieving the separation of chiral molecules, enzyme enhanced ultrafiltration (EEUF), a new method based on polymer enhanced ultrafiltration (PEUF), utilizing apoenzymes as ligands, was developed. Benzoin was chosen as the model chiral molecule. Bovine serum albumin (BSA) and apo form of benzaldehyde lyase (BAL) (E.C. 4.1.2.38) were used as chiral ligands in PEUF and EEUF experiments, respectively. In order to bind to the target enantiomer well, the addition of ligand to the benzoin solution...
Concise design and synthesis of pyridine-fused heterocycles via 6 pi- Azaelectrocyclization process of iminoalkyne derivatives
Sendil, Kivilcim; Keskin, Selbi; Balcı, Metin (Elsevier BV, 2019-11-15)
A concise and regioselective approach to the synthesis of pyridine-fused heterocycles and benzoxazepine derivatives was developed. Propargyl imines derived from aromatic aldehydes and propargyl amine underwent 6 pi-electrocyclization reactions at high temperatures in high yields to form pyridine-fused heterocycles. Application of the same methodology to aromatic imines having a hydroxyl group in the ortho position resulted in the formation of (benz)oxazepine derivatives. The formation mechanism of the produ...
Citation Formats
E. Hoplamaz, “Development of a new method for the synthesis of benzo[h][1,6]naphthyridine derivatives and chromenopyrazinone skeleton,” M.S. - Master of Science, Middle East Technical University, 2015.
METU IIS - Integrated Information Service open@metu.edu.tr