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Relevant academic research and scientific papers

Ruthenium(II)a€“carbonyl complexes containing two N-monodentate 1,8-naphthyridine ligands: active catalysis in transfer hydrogenation reactions

The reaction of 2-aminonicotinaldehyde with 2- or 4-methoxyacetophenone in basic media leads to the new ligands 2-(4-methoxyphenyl)-1,8-naphthyridine and 2-(2-methoxyphenyl)-1,8-naphthyridine, respectively, in high yield. The reaction of these naphthyridi

Sustainable synthesis of N-heterocycles in water using alcohols following the double dehydrogenation strategy

The present study describes the first example of synthesis of pharmaceutically relevant N-heterocycles like substituted quinolines, acridines and 1,8-naphthyridines in water under air using alcohols in presence of a new water soluble Ir-complex. The viability and efficiency of this approach was demonstrated by the efficient synthesis of biologically active natural product (±)-galipinine and gram scale synthesis of various N-heteroaromatics. Several kinetic experiments and DFT calculations were carried out to support the plausible reaction mechanism which disclosed that this system followed a concerted outer sphere mechanism for the dehydrogenation of alcohols.

Catalytic activity in transfer hydrogenation using ruthenium (II) carbonyl complexes containing two 1,8-naphthyridine as N-monodentate ligands

A new series of novel complexes of type cis-[Ru(CO)2Cl2(L)2], L = 2-phenyl-1,8-naphthyridine, 2-(4′-nitrophenyl)-1,8-naphthyridine, 2-(4′-bromophenyl)-1,8-naphthyridine, 2-(4′-methylphenyl)-1,8-naphthyridine, 2-(3′-methoxyphenyl)-1,8-naphthyridine, 2-(2′-methoxyphenyl)-1,8-naphthyridine and 2-(4′-methoxyphenyl)-1,8-naphthyridine have been successfully synthesized and characterized. We found that the complexes can be directly synthesized from [RuCl2(CO)2]2 with high yield. The crystallographic structures of complex cis-[RuCl2(CO)2(2-(4′-methoxyphenyl)-1,8-naphthyridine-κN8)2] and cis-[RuCl2(CO)2(2-(2′-methoxyphenyl)-1,8-naphthyridine-κN8)2] have been established by X-ray single crystal diffraction studies, which indicate an octahedral geometry with two 1,8-naphthyridine ligands coordinated to the metal in a N-monodentate fashion. The ruthenium(II) complexes have been studied as catalysts in the transfer hydrogenation of acetophenone. We found that complexes show moderate activities and a 100% selectivity. The best turnover frequency (390 h?1) is found for cis-[RuCl2(CO)2(2-(4′-methoxyphenyl)-1,8-naphthyridine-κN8)2] when the substrate/catalysis ratio was 1000/1. The catalytic conditions were optimized using different substrate/catalyst and base/catalyst ratios.

Direct Access to Nitrogen Bi-heteroarenes via Iridium-Catalyzed Hydrogen-Evolution Cross-Coupling Reaction

Through cooperative actions of iridium catalyst and NaOTf additive we report a new direct access to nitrogen bi-heteroarenes via hydrogen-evolution cross-coupling of the β-site of indoles/pyrrole with the α-site of N-heteroarenes. The reaction proceeds in an atom- and redox-economic fashion together with the merits of an easily available catalyst system, broad substrate scope, excellent functional tolerance, and no need for external oxidants, offering a practical way to create π-conjugated systems.

Synthesis of 1,8-naphthyridines from 2-aminonicotinaldehydes and terminal alkynes

A copper(II) triflate-catalyzed diethylamine-assisted protocol for the reaction of 2-aminonicotinaldehydes and terminal alkynes leading to 1,8-naphthyridines is described. The overall process presumably involves a copper(II) triflate-catalyzed hydroaminat

Hydrogen-Transfer-Mediated Direct β-Alkylation of Aryl-1,8-naphthyridines with Alcohols under Transition Metal Catalyst Free Conditions

By employing abundant and sustainable alcohols as the alkylating reagents, a new and direct alkylation method has been demonstrated. This method enables the selective alkylation of the less substituted pyridyl ring at the β-site of aryl-1,8-naphthyridines

Ruthenium-Catalyzed Enantioselective Hydrogenation of 1,8-Naphthyridine Derivatives

The first asymmetric hydrogenation of 2,7-disubstituted 1,8-naphthyridines catalyzed by chiral cationic ruthenium diamine complexes has been developed. A wide range of 1,8-naphthyridine derivatives were effectively hydrogenated to give 1,2,3,4-tetrahydro-1,8-naphthyridines with up to 99% ee and full conversions. The method provides a practical and facile approach to the preparation of valuable chiral heterocyclic building blocks and useful motifs for a new kind of P,N-ligand.

Understanding C-H bond activation on a diruthenium(I) platform

Activation of the C-H bond at the axial site of a [RuI-Ru I] platform has been achieved. Room-temperature treatment of 2-(R-phenyl)-1,8-naphthyridine (R = H, F, OMe) with [Ru2(CO) 4(CH3CN)6

Microwave assisted synthesis of 1,8- naphthyridines

A highly efficient and practical methodology for the synthesis of 2-aryl-1.8-naphthyridines 3 is described starting from 2-aminonicotinaldehyde 1 and various acetophenones under microwave conditions.

Substituted 1,8-Naphthyridines: Part VI - Synthesis of 3-Aroyl-2-phenyl-1,8-naphthyridines

The condensation of 2-aminonicotinaldehyde (1) with ω-benzoylacetophenones (2) leads to either 3-aroyl-2-phenyl-1,8-naphthyridines (3) in the presence of gl. acetic acid containing a catalytic amount of conc.H2SO4, or to 2-aryl-1,8-naphthyridines (4) in e