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

Hoplamaz, Emre
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.


Enhancing electrochemical and electrochromic performances of carbazole comprising monomer via copolymerization with 3,4-ethylenedioxythiophene (EDOT)
Kalay, Isil; Yigit, Deniz; GÜLLÜ, Mustafa; DEPCİ, TOLGA; Toppare, Levent Kamil; Hacioglu, Serife O. (Elsevier BV, 2020-09-01)
In this study, two novel electrochromic copolymers (CoP1.3 and CoP1.5) were synthesized via electrochemical methods and characterized. The comonomers used in the synthesis were 3,4-ethylenedioxythiophene (EDOT) and a carbazole comprising monomer; 9-(2-(4-(Phenyldiazenyl) phenoxy) ethyl)-3,6-di(thiophen-2-yl)-9H-carbazole (M1). Carbazole containing monomer (M1) and EDOT were combined with two different comonomer feed ratios, 1: 3 and 1: 5 respectively in order to investigate the effect of increasing EDOT amo...
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 ...
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. 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...
Recent progress in asymmetric synthesis of aziridine derivatives (microreview)
Doğan, Özdemir (Springer Science and Business Media LLC, 2018-04-01)
This microreview describes recent advances in asymmetric synthesis of aziridine derivatives, which have been published over the last two years.
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.