Synthesis of 2,6-naphthyridine

Giacomello, G.; Gualtieri, Fulvio; Riccieri, F. M.; Stein, Mario

doi:10.1016/s0040-4039(00)90042-x

Cited by 26 publications

(4 citation statements)

References 3 publications

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“…The experimental direct dipole coupling constants are given in Table 1. Iteration upon the indirect dipole coupling constants, Jq, gave values which agreed, within experimental error, with literature values obtained from isotropic spectra (10)(11)(12)(13). For 1,5-naphthyridine the rms deviation between calculated and experimental line positions was 1.1 Hz for 90 lines and for 2,6-naphthyridine the rms deviation was 2.4 Hz for 119 lines.…”

Section: Resultssupporting

confidence: 82%

Nematic phase nuclear magnetic resonance studies of the structure and orientation of 1,5- and 2,6-naphthyridines

Lee¹,

Gilson²

1976

Can. J. Chem.

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The proton magnetic resonance spectra of 1,5- and 2,6-naphthyridine dissolved in the nematic liquid crystal MBBA have been analysed. The proton geometries do not give good fits to the ring skeleton structure but it appears that the carbon–hydrogen bond lengths are not all of equal length and the bond angles indicate some bending of the C—H bonds toward the adjacent nitrogen atom. The probability functions for orientation of diazanaphthalenes in nematic solvents show that nitrogen atoms in the ring framework affect the direction of principal orientation, which does not follow either the maximum molecular dimension or the inertial axis.

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Section: Resultssupporting

confidence: 82%

Nematic phase nuclear magnetic resonance studies of the structure and orientation of 1,5- and 2,6-naphthyridines

Lee¹,

Gilson²

1976

Can. J. Chem.

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“…However, the synthesis of 2,6-naphthyridine has proven to be highly challenging. Since its original synthesis in 1965, only a few documented techniques exist. − Currently, the available synthetic methods for 2,6-naphthyridine typically begin with multisubstituted pyridine as the starting material, involving lengthy synthesis steps and exhibiting poor reaction efficiency. This hinders the postmodification of the skeletons and restricts the diversity of molecular structures, thereby obstructing the exploration of potential applications for 2,6-naphthyridine.…”

Section: Introductionmentioning

confidence: 99%

Unlocking Structurally Nontraditional Naphthyridine-Based Electron-Transporting Materials with C–H Activation–Annulation

Luo,

Bao,

Liu

et al. 2024

J. Am. Chem. Soc.

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The inherent benefits of C−H activation have given rise to innovative approaches in designing organic optoelectronic molecules that depart from conventional methods. While theoretical calculations have suggested the suitability of the 2,6-naphthyridine scaffold for electron transport materials (ETMs) in organic lightemitting diodes (OLEDs), the existing synthetic methodologies have proven to be insufficient for the construction of multiple arylated and fully aryl-substituted molecules. Herein, we present a solution for the synthesis of 2,6-naphthyridine derivatives, with the rhodium-catalyzed consecutive C−H activation−annulation process of fumaric acid with alkynes standing as the pivotal step within this strategy. The ETMs, purposefully designed and synthesized based on the 2,6-naphthyridine framework, exhibit an impressively high glass-transition temperature (T g ) of 282 °C and high electron mobility (μ e ), setting a new benchmark for ETMs in OLEDs with a μ e exceeding 10 −2 cm 2 V −1 s −1 . These materials prove to be versatile ETM candidates suitable for red, green, and blue phosphorescent OLED devices.

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“…Six different naphthyridine systems ( fig. 1), namely 1, 5-Naphthyridine (1) 1, 6-Naphthyridine (2) 1, 7-Naphthyridine (3) 1, 8-Naphthyridine (4) 2,6-Naphthyridine (5) and 2, 7-Naphthyridine (6) are existing at the present time and amongst them 1, 8-Naphthyridine is the novel class of heterocycle [3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Recent Developments and Multiple Biological Activities Available With 1, 8-Naphthyridine Derivatives: A Review

Gurjar¹,

Pal²

2019

Int J Pharm Pharm Sci

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Within the wide range of nitrogen-containing heterocyclic compounds, the derivatives of 1,8-naphthyridine (NPTR) have gained a rising interest due to their reported versatile biological activities. The derivatives of NPTR scaffold are found to invite special interest from researchers nowadays on the significance of their manifestations of multiple attractive pharmacological activities which establish them as an effective and versatile tool in pharmaceutical chemistry and drug discovery. The diverse biological activities mainly include anti-inflammatory, antimicrobial, antiviral, anticancer, antihypertensive and analgesic activities. Novel NPTR scaffold has emerged its potency to treat neurological diseases like depression and Alzheimer's disease. Further these agents possess different inhibitory activities, such as anti-HIV, anti-osteoporotic, αvβ3 antagonism, antimalarial, platelet aggregation, anti-oxidant, anti-allergic, gastric antisecretory, anticonvulsant, epidermal growth factor receptor (EGFR) inhibition, protein kinase inhibition, ionotropic properties, β3 antagonism, phosphodiesterase 4 (PDE 4) inhibitions, adenosine receptor agonistic activity, adrenoceptors antagonism and DNA stabilizing activity, etc. In this review, we highlight the updates of different 1,8-naphthyridine derivatives and explain the key data available in the context of various biological activities of NPTR derivatives available from the literature. This may direct opportunity in researches in the synthesis of novel medicinal agents and the development of new heterocycles for modification of existing biological actions as well as evaluation of other possible pharmacological activities.

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Synthesis of 2,6-naphthyridine

Cited by 26 publications

References 3 publications

Nematic phase nuclear magnetic resonance studies of the structure and orientation of 1,5- and 2,6-naphthyridines

Nematic phase nuclear magnetic resonance studies of the structure and orientation of 1,5- and 2,6-naphthyridines

Unlocking Structurally Nontraditional Naphthyridine-Based Electron-Transporting Materials with C–H Activation–Annulation

Recent Developments and Multiple Biological Activities Available With 1, 8-Naphthyridine Derivatives: A Review

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