BIOMAT Database Logo BIOMAT Database Logo

Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED. 2022

Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia.

Oxidative cyclization is one of the most significant reactions in organic synthesis. Naphthyridine derivatives are often used as luminescence materials in molecular recognition because of their rigid planar structure and as new drugs. Organic light-emitting diodes (OLEDs) have rapidly grown as one of the leading technologies for full-color display panels and eco-friendly lighting sources. In this work, we propose the synthesis of previously unknown benzo[b]chromeno[4,3,2-de][1,6]naphthyridines via intermolecular oxidative cyclization of 5-(2-hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines in formic acid. The investigation of the reaction mechanism using 1H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized benzo[b]chromeno[4,3,2-de][1,6]naphthyridines was confirmed by 2D-NMR spectroscopy. Such a rigid geometry of synthesized compounds is desired to minimize non-radiative energy losses in OLEDs. The quantum chemical calculations are also presented in the study.

UI MeSH Term Description Entries
D009287 Naphthyridines A group of two-ring heterocyclic compounds consisting of a NAPHTHALENES double ring in which two carbon atoms, one per each ring, are replaced with nitrogens.
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D003201 Computers Programmable electronic devices designed to accept data, perform prescribed mathematical and logical operations at high speed, and display the results of these operations. Calculators, Programmable,Computer Hardware,Computers, Digital,Hardware, Computer,Calculator, Programmable,Computer,Computer, Digital,Digital Computer,Digital Computers,Programmable Calculator,Programmable Calculators
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018384 Oxidative Stress A disturbance in the prooxidant-antioxidant balance in favor of the former, leading to potential damage. Indicators of oxidative stress include damaged DNA bases, protein oxidation products, and lipid peroxidation products (Sies, Oxidative Stress, 1991, pxv-xvi). Anti-oxidative Stress,Antioxidative Stress,DNA Oxidative Damage,Nitro-Oxidative Stress,Oxidative Cleavage,Oxidative DNA Damage,Oxidative Damage,Oxidative Injury,Oxidative Nitrative Stress,Oxidative Stress Injury,Oxidative and Nitrosative Stress,Stress, Oxidative,Anti oxidative Stress,Anti-oxidative Stresses,Antioxidative Stresses,Cleavage, Oxidative,DNA Damage, Oxidative,DNA Oxidative Damages,Damage, DNA Oxidative,Damage, Oxidative,Damage, Oxidative DNA,Injury, Oxidative,Injury, Oxidative Stress,Nitrative Stress, Oxidative,Nitro Oxidative Stress,Nitro-Oxidative Stresses,Oxidative Cleavages,Oxidative DNA Damages,Oxidative Damage, DNA,Oxidative Damages,Oxidative Injuries,Oxidative Nitrative Stresses,Oxidative Stress Injuries,Oxidative Stresses,Stress Injury, Oxidative,Stress, Anti-oxidative,Stress, Antioxidative,Stress, Nitro-Oxidative,Stress, Oxidative Nitrative,Stresses, Nitro-Oxidative

Related Publications

Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Unexpected behavior of enaminones: interesting new routes to 1,6-naphthyridines, 2-oxopyrrolidines and pyrano[4,3,2-de][1,6]naphthyridines.
December 2012, Molecules (Basel, Switzerland),
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Synthesis and anti-HSV-1 evaluation of new 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridines and 3H-pyrido[2,3-b]pyrazolo[3,4-h]-1,6-naphthyridines.
February 2012, Organic and medicinal chemistry letters,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Synthesis and characteristics of novel fluorescence dyes based on chromeno[4,3,2-de][1,6]naphthyridine framework.
February 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Design, synthesis, and pharmacological evaluation of [1, 3] dioxolo-chromeno[2,3-b]pyridines as anti-seizure agents.
August 2023, Molecular diversity,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
DMSO-assisted environmentally benign synthesis of benzo[c]-chromeno[4,3,2-gh]phenanthridines by remote oxidative hetero cross-coupling cyclization and aromatization reaction.
May 2022, Chemical communications (Cambridge, England),
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Synthesis and cytotoxic activity of carboxamide derivatives of benzo[b][1,6]naphthyridines.
March 2003, Journal of medicinal chemistry,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Dihydro-pyrano[2,3-b]pyridines and tetrahydro-1,8-naphthyridines as CB1 receptor inverse agonists: synthesis, SAR and biological evaluation.
June 2010, Bioorganic & medicinal chemistry letters,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Development of 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors.
October 2018, Bioorganic & medicinal chemistry,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Unravelling the anticancer potential of functionalized chromeno[2,3-b]pyridines for breast cancer treatment.
July 2020, Bioorganic chemistry,
Yuliya E Ryzhkova, and Fedor V Ryzhkov, and Artem N Fakhrutdinov, and Michail N Elinson
Synthesis and DNA binding properties of novel benzo[b]isoquino[2,3-h]-naphthyridines.
August 2005, Organic & biomolecular chemistry,
Copied contents to your clipboard!