Naphthyridine chemistry. V. One-step synthesis of 1,8-naphthyridines

Paudler, William W.; Kress, Thomas J.

doi:10.1021/jo01278a078

Cited by 66 publications

(20 citation statements)

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“…Materials Quinoline, isoquinoline, acridine, phthalazine, quinazoline, and quinoxaline were obtained commercially. 1,s-Naphthyridine ( 25), 1,6-naphthyridine (47), 1,8-naphthyridine (48). and 3-nitroquinoline (49) were synthesized as described in the literature.…”

Section: Methodsmentioning

confidence: 99%

Quaternary Nitrogen Heterocycles. I. Equilibrium and Spectral Data for Pseudobase Formation by the N-Methyl Cations of Diazanaphthalenes

Bunting¹,

Meathrel²

1972

Can. J. Chem.

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Equilibrium constants have been measured at 25° for the formation of pseudobases from the 2-methyl-phthalazinium, 1-methylquinoxalinium, 1-methyl- 1,5-naphthyridinium, 6-methyl-1,6-naphthyridinium, 7-methyl-1,7-naphthyridinium, 1-methyl-1,8-naphthyridinium, 1-methyl-3-nitroquinolinium, and 2-methyl-4-nitroisoquinolinium cations. Ionization constants have also been obtained for ionization of some of these pseudobases to alkoxide anions. For each cation the site of hydroxide attack has been determined by comparison of the u.v. and p.m.r. spectra of the pseudobases, the corresponding methoxide adducts, and the lithium aluminum hydride reduction products. In all cases, except for the 1-methylquinoxalinium cation, only one major pseudobase species is present in solution, and ring-opening does not occur to any appreciable extent. The pseudobase of the 1-methylquinoxalinium cation exists in equilibrium with a considerable amount of its covalent hydrate from addition of water across the C3—N4 bond.

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Section: Methodsmentioning

confidence: 99%

Quaternary Nitrogen Heterocycles. I. Equilibrium and Spectral Data for Pseudobase Formation by the N-Methyl Cations of Diazanaphthalenes

Bunting¹,

Meathrel²

1972

Can. J. Chem.

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“…The recently developed facile syntheses of some naphthyridines (1)(2)(3)(4) has made these rji:g systems available to extensive examinations of their reactivities. Among these studies, the electrophilic substitution reactions, Chichibabin amination (5), and behavioral patterns of the N-oxides (6-8) have been the subject of previous papers.…”

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confidence: 99%

Naphthyridine Chemistry. XVII: Di-N-alkylated Naphthyridines

Pokorný¹,

Paudler²

1973

Can. J. Chem.

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It has been shown that the N,Nf-dimethylated naphthyridines form pseudo bases by hydroxide addition in the quinolinoid rather than the isoquinolinoid ring, where possible.The charge repulsion in the 1,8-dimethyl-1,8-naphthyridinium ion is reflected by its facile partial conversion to a mono-pseudo base at room temperature. A variable temperature study of this equilibrium reaction is described.On a demontre que les naphthyridines dimethylees en position N , N ' forment, si possible, des pseudobases par l'addition d'un groupement hydroxyle au cycle quinolinoide plutbt qu'au cycle isoquinolinoide.La repulsion des charges dans l'ion dimethyl-1,8 naphthyridinium-1,8 est mise en Cvidence par sa conversion facile et partielle en une mono pseudo-base a la temperature ambiante. Une etude a diverses temperatures de cette reaction d'equilibre est aussi decrite.

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“…The classical procedure [21] used to prepare 1,8-naphthyridine contemplates the condensation of anhydrous glycerol with the aromatic ring of 2-aminopyridine in the presence of an oxidizing mixture called the Utermohlen's "sulfo-mix". [22] This mixture is constituted by 3-nitrobenzensulphonic acid and concentrated sulfuric acid, and is the product of the sulfonation of nitrobenzene with oleum (20 %, H 2 SO 4 /SO 3 ).…”

Section: Resultsmentioning

confidence: 99%

“…[21] Sodium 3-nitrobenzensulfonate (40 g, 0.178 mol) was dissolved in concd H 2 SO 4 (50 mL), and the resulting solution was treated with anhyd glycerol (25 g, 0.271 mol) and stirred vigorously to obtain homogeneity. The resulting mixture was treated with 2-aminopyridine (7.5 g, 0.08 mol) and stirred in an oil bath at 130 8C for 5 h, then cooled in an ice bath and made alkaline by addition of concd NaOH.…”

Section: 8-naphthyridine (Naph)mentioning

confidence: 99%

Monofunctional Platinum(II) Complexes with Potent Tumor Cell Growth Inhibitory Activity: The Effect of a Hydrogen‐Bond Donor/Acceptor N‐Heterocyclic Ligand

et al. 2014

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In this paper we investigate the possibility of further increase the role of the N-donor aromatic base in antitumor Hollis-type compounds by conferring the possibility to act as a hydrogen-bond donor/acceptor. Therefore, we synthesized the Pt(II) complex cis-[PtCl(NH3 )2 (naph)]NO3 (1) containing the 1,8-naphthyridine (naph) ligand. The naphthyridine ligand is generally monodentate, and the second nitrogen atom can act as H-bond donor/acceptor depending upon its protonation state. The possibility of forming such an H-bond could be crucial in the interaction of the drug with DNA or proteins. Apart from the synthesis of the compound, in this study we evaluated its in vitro antitumor activity in a wide panel of tumor cell lines, also including cells selected for their sensitivity/resistance to oxaliplatin, which was compared with that of previously reported complex 2 ([PtI(2,9-dimethyl-1,10-phenanthroline)(1-methyl-cytosine)]I) and oxaliplatin and cisplatin as reference compounds. The cytotoxicity data were correlated with the cellular uptake and the DNA platination levels. Finally, the reactivity of 1 towards guanosine 5'-monophosphate (5'-GMP) and glutathione was investigated to provide insights into its mechanism of action.

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Naphthyridine chemistry. V. One-step synthesis of 1,8-naphthyridines

Cited by 66 publications

References 0 publications

Quaternary Nitrogen Heterocycles. I. Equilibrium and Spectral Data for Pseudobase Formation by the N-Methyl Cations of Diazanaphthalenes

Quaternary Nitrogen Heterocycles. I. Equilibrium and Spectral Data for Pseudobase Formation by the N-Methyl Cations of Diazanaphthalenes

Naphthyridine Chemistry. XVII: Di-N-alkylated Naphthyridines

Monofunctional Platinum(II) Complexes with Potent Tumor Cell Growth Inhibitory Activity: The Effect of a Hydrogen‐Bond Donor/Acceptor N‐Heterocyclic Ligand

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