Advances in the Chemistry of Naphthyridines

Литвинов, В. П.

doi:10.1016/s0065-2725(06)91004-6

Cited by 75 publications

(23 citation statements)

References 396 publications

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“…Benzo[ f ][1,7]naphthyridines [1] (Figure 1) are naturally occurring [2,3] and synthetic benzo-fused bis -heterocyclic systems [4], which have been of high interest for synthetic community from many years ago, mainly due to their interesting properties in various fields of science, such as optics [5]. However, their main application lies in the medicinal chemistry because some bioactive compounds are based on the benzo[ f ][1,7]naphthyridine core.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization

et al. 2018

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A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before.

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Section: Introductionmentioning

confidence: 99%

Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization

et al. 2018

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“…Naphthyridines provide an important scaffold for a variety of compounds of unique biological activities. Their synthesis, properties, reactivity and biological activity are covered in several reviews [15][16][17]. The synthetic use of the Friedländer reaction for preparation of 1,7-naphthyridines (III) has, however, been limited by the inconvenient preparation methods for the necessary 2-amino carbonyl compounds, such as 3-aminoisonicotinaldehyde (13) [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 1,7‐naphthyridines by Friedländer condensation of pyridine substrates

Stockmann

Fiksdahl

2011

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).The general ability of appropriate pyridyl compounds (aldehyde or ketone) to undergo Friedländer condensation to give different 1,7-naphthyridines has been demonstrated. 2,4-Disubstituted 1,7-naphthyridine 8 was prepared from 3-amino-4-acetylpyridine (6) and ketone 4 (82%). The Friedländer self-condensation of pyridyl substrate 6 is reported, as well. The dimer product, 2-(3-aminopyridin-4-yl)-4-methyl-1,7-naphthyridine (7), was obtained in 97% yield. 2-Aryl-and 2,3-diaryl-1,7-naphthyridines (16-18) were prepared from 3-aminoisonicotinaldehyde (13) and arylketones 4, 14, and 15 (28-71%). The key substrates 6 and 13 are readily available via the improved pyridine nitration method.

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“…Considerable efforts have been directed toward the synthesis of 1.6-naphthyridine derivatives. A number of methods for their preparations have been developed and are well covered in the literature by some excellent reviews [6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

“…Much greater attention has been directed towards the synthesis of benzo-and pyrido-annelated 1,6-naphthyridine ring systems probably as a consequence of the ready availability of suitable precursors [8][9][10]. At the same time only two azole[h]annelated ring systems have been reported, namely oxazolo [4,5-f] [1,6]naphthyridine [11] and pyrazolo [3,4-h] [1,6]naphthyridine [12][13][14].…”

Section: Introductionmentioning

confidence: 99%