Pyridopyridines

Литвинов, В. П.; Roman, S. V.; Dyachenko, V. D.

doi:10.1070/rc2001v070n04abeh000617

Cited by 36 publications

(17 citation statements)

References 111 publications

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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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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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“…Several reviews have appeared in the area of naphthyridines [ 1 , 2 , 3 , 4 ] including some references to fused 1,5-naphthyridines. Among them, in 2005, Ivanov et al [ 5 ] published a generic review on benzo[ b ]naphthyridines.…”

Section: Introductionmentioning

confidence: 99%

Fused 1,5-Naphthyridines: Synthetic Tools and Applications

et al. 2020

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Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified according to the nature of the cycle fused to the 1,5-naphthyridine ring: carbocycles, nitrogen heterocycles, oxygen heterocycles, and sulphur heterocycles. In addition, taking into account the aforementioned versatility of these heterocycles, their reactivity is presented as well as their use as a ligand for metal complexes formation. Finally, those fused 1,5-naphthyridines that present biological activity and optical applications, among others, are indicated.

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“…Studies in the literature reveal that many of the benzo[c] [2,7] naphthyridine derivatives [17][18][19][20][21] have been synthesized employing new strategies to investigate the potential of fused ve membered heterocycles such as isoxazolo-, 22 cyclopenta-, 23 pyrazolo-, 24 imidazo- 25 and furo- 26,27 annulated 2,7-naphthyridines. Numerous reported elegant reactions that oen involved multistep harsh reaction conditions using organic solvents and homogenous or heterogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%