254-79-5

Usage

Chemical Properties

off-whtie solid

Purification Methods

Purify 1,5-naphthyridine by repeated sublimation. The picrate crystallises from EtOH with m 200o(dec). [UV: Armarego Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 133 1971, Beilstein 23 II 178, 23 III/IV 1235.]

InChI:InChI=1/C8H6N2/c1-3-7-8(9-5-1)4-2-6-10-7/h1-6H

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 56-81-5 glycerol 
• 198549-12-1 4-(2-phenyl-1H-imidazol-1-yl)butanenitrile 
• 791856-59-2 4-(2-phenylimidazol-1-yl)thiobutyramide 
• 198549-21-2 3-(3-(2-phenylimidazol-1-yl)propyl)-1,2,4-triazine 

Downstream Products

• 27305-48-2 1,5-naphthyridine N-⁽¹⁾-oxide 
• 27305-49-3 1,5-naphthyridine 1,5-dioxide 
• 17965-80-9 2-amino-1,5-naphthyridine 
• 13993-61-8 1.1,2,3,4-tetrahydro-1,5-naphthyridine 
• 52831-33-1 ortho -2 ethyl, benzanilide 
• 108958-67-4 [2-(1H-Indol-3-yl)-2H-[1,5]naphthyridin-1-yl]-phenyl-methanone 
• 87505-10-0 1a,1b,2,7b-tetrahydro-1,2-bis(phenylsulfonyl)-1H-azirino<1.2-a>cyclopropa<1.5>naphthyridine 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 27017-66-9 2,6-dichloro-1,5-naphthyridine 
• 13623-79-5 1,5-diaza-trans-decalin 
• 13623-83-1 1,5-diaza-cis-decalin 
• 17965-72-9 3,7-dibromo-1,5-naphthyridine 
• 17965-71-8 3-bromo-1,5-naphthyridine 

Relevant academic research and scientific papers

New Tricks by Old Anions: Hydrogen Bonded Hexacyanoferrous Anionic Networks

Hexacyanoferrates are well-known to form metal?organic frameworks by coordination to metal atoms or acting as hydrogen bond acceptors. In this paper we report a new type of hexacyanoferrate self-assembly, based on direct hydrogen bonding of partially protonated hexacyanoferrate anions. By preparing a series of 15 hexacyanoferrates with various organic bases, we have found that protonated hexacyanoferrates (present in 10 structures) readily form chains (two structures), two-dimensional (four structures), or three-dimensional networks (four structures), whereby the dimensionality of the network generally increases with the protonation degree of the hexacyanoferrates. The exact mode of the self-assembly, including the network type, depends on fine interplay of the pKa value of the base, its steric properties, and the stoichiometry of the formed solid.

Linear-shaped thermally activated delayed fluorescence emitter using 1,5-naphthyridine as an electron acceptor for efficient light extraction

In this study, we developed a donor-π-acceptor-π-donor-type thermally activated delayed fluorescence (TADF) emitter (NyDPAc) using 1,5-naphthyridine as a core moiety. NyDPAc exhibited a high horizontal dipole ratio and thus a high external quantum efficiency (20.9%) even at a relatively low photoluminescence quantum yield (57%). 1,5-naphthyridine as an electron acceptor represents a promising core moiety for efficient TADF materials.

Electrochemical investigation of structurally varied azinium scaffolds

Inspired by the successful utilization of aziniums as anolytes in redox-flow batteries, we have designed and prepared a systematically extended series of (di)azinium compounds based on pyrazine, bipyridine, 1,5-naphthyridine, 3,8-phenanthroline, (E)-4,4′-

One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes

The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.

Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl)

A set of successive regioselective metalations and functionalizations of the 1,5-naphthyridine scaffold are described. A combination of Zn-, Mg-, and Li-TMP (TMP=2,2,6,6-tetramethylpiperidyl) bases and the presence or absence of a Lewis acid (BF3?OEt2) allows the introduction of up to three substituents to the 1,5-naphthyridine core. Also, a novel “halogen dance” reaction was discovered upon metalation of an 8-iodo-2,4-trifunctionalized 1,5-naphthyridine allowing a fourth regioselective functionalization. Additionally, reactions leading to key 1,5-naphthyridines for the preparation of OLED materials and a potential antibacterial agent were performed.

Design and synthesis of novel substituted naphthyridines as potential c-Met kinase inhibitors based on MK-2461

Abstract Two series of novel 1,5-naphthyridine and 1,6-naphthyridine derivatives were designed and synthesized based on the c-Met kinase inhibitor MK-2461 under the guidance of scaffold hopping strategy. All were tested on c-Met kinase and in vitro anti-tumor activities against Hela and A549 cell lines. The results indicated that 1,6-naphthyridine was a more promising c-Met inhibitory structure core compared with 1,5-naphthyridine. Among them, 26b and 26c showed the best enzymic and cytotoxic activities. The western blot experiments implied that the cytotoxic activity of 26c might be partially through suppressing the phosphorylation of c-Met kinase.

Iodine- and indium(III) chloride-catalyzed facile syntheses of 1,5- and 1,8-naphthyridines

Iodine- and InCl3-catalyzed facile syntheses of 1,5- and 1,8-naphthyridines from 3-aminopyridine and 2-aminopyridines are described. The catalyst InCl3 could be recovered and reused up to five times efficiently.

Intramolecular inverse-electron-demand Diels-Alder reactions of imidazoles with 1,2,4-triazines: A new route to 1,2,3,4-tetrahydro-1,5-naphthyridines and related heterocycles

The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.

Unusual oxidative rearrangement of 1,5-diazadecalin

Upon treatment with (PhIO)n or PhI(OAc)2, 1,5-diaza-cis-decalin undergoes oxidation at the more hindered position along with fragmentation to yield the ring-expanded bislactam. The cis and trans 1,5-diazadecalins both undergo the sam

Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation-substitution

(equation presented) A short, efficient synthesis of chiral 1,5-diaza-cis-decalins (7) is presented. In the lithiation of N-Boc pyrrolidine, the ligands with the smallest most electron rich R groups (Me > Et > CH2tBu > CH2CF3 ≈ Bn) were most effective. In the asymmetric deprotonation/substitution of benzylic substrates, (R,R)-7 (R = Me, R′ = H) conferred modest selectivity. The ready availability of both enantiomers of the 1,5-diaza-cis-decalins and the ability to tune steric and electronic properties renders these compounds an attractive new class of diamine ligands.