Azines: synthesis, structure, electronic structure and their applications

Chourasiya, Sumit S.; Kathuria, Deepika; Wani, Aabid Abdullah; Bharatam, Prasad V.

doi:10.1039/c9ob01272a

Cited by 62 publications

(41 citation statements)

References 238 publications

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“…Synthesis of these compounds attracts great attention to organic chemists, due to their reactivity and a wide spectrum of both biological and therapeutic activities. A similar trend is seen for azines, compounds formed by the reaction of two different or the same carbonyl compounds (mostly aldehydes or ketones) with hydrazine (Safari & Gandomi-Ravandi, 2014;Chourasiya et al, 2019). The chemical properties and biological activities of these compounds mostly are the consequence of the presence of double bonds and nitrogen atoms.…”

Section: Introductionmentioning

confidence: 52%

Synthesis, complete assignment of 1H- and 13C-NMR spectra and antioxidant activity of new azine derivative bearing coumarin moiety

Ristić¹,

Dekić²,

Radulović³

et al. 2021

Bull Nat Sci Research

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In this research, the synthesis of a new azine derivative with coumarin moiety was performed in three reaction steps, starting from 4-hydroxycoumarin. The first step in synthesis was the acetylation of 4-hydroxycoumarin to yield 3-acetyl-4-hydroxycoumarin and then the obtained 3-acetyl-4-hydroxycoumarin was reacted with hydrazine hydrate and give a corresponding hydrazone. Condensation of the hydrazone with 4-ethoxy-3-methoxybenzaldehyde afforded the target compound 1-[1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-ethylidene]-2-(4-etoxy-3-methoxybenzylidene)-hydrazine in a good yield. The resulting azine derivative is fully spectrally characterized, including complete assignment of 1H- and 13C-NMR spectra, as well as 2D NMR (1H-1H COSY, NOESY, HSQC and HMBC) spectra. The antioxidant activity of corresponding hydrazone and target compound was evaluated by DPPH method where hydrazone derivative displayed a significant and target azine good antioxidant activity, with IC50 (μM) values 11.69 and 216.60, respectively.

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Section: Introductionmentioning

confidence: 52%

Synthesis, complete assignment of 1H- and 13C-NMR spectra and antioxidant activity of new azine derivative bearing coumarin moiety

Ristić¹,

Dekić²,

Radulović³

et al. 2021

Bull Nat Sci Research

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“…On the other hand, azaheterocycles are emerging as crucial privileged scaffolds in modern medicinal chemistry and drug discovery, a large variety of biological activities being described for these compounds, such as: antibacterial, antifungal, antitubercular, antiviral, antiplasmodial, antimalarial, anticancer, anti-inflammatory, antihypertensive, diuretics, antithrombics, anticoagulants, antidepressant, anxiolytics, anticonvulsant, analgesic, etc. [11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

et al. 2020

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Microwave (MW) assisted reactions have became a powerful tool in azaheterocycles chemistry during the last decades. Five and six membered ring azaheterocycles are privileged scaffolds in modern medicinal chemistry possessing a large variety of biological activity. This review is focused on the recent relevant advances in the MW assisted reactions applied to azaheterocyclic derivatives and their medicinal chemistry applications from the last five years. The review is divided according to the main series of azaheterocycles, more precisely 5- and 6-membered ring azaheterocycles (with one, two, and more heteroatoms) and their fused analogues. In each case, the reaction pathways, the advantages of using MW, and considerations concerning biological activity of the obtained products were briefly presented.

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“…These compounds have been recently used as nonlinear optical (NLO) materials, 9 conducting materials, 10 as ion-selective optical sensors, 11 and in supramolecular chemistry. 12,13 Furthermore, azines act as beneficial candidates for drug development in pharmacological industries possess and some derivatives displayed antifungal, anticancer, antihypertensive, antibacterial, antimicrobial activities 14 (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Azines (2,3-diaza-1,3-butadienes) of the formula R 1 R 2 CN–NCR 1 R 2 are a functional class of compounds that demonstrate a wide array of chemical, physical, and biological applications because of their distinctive structural and stereochemical properties . Azines have proven to be very useful in investigating metal-mediated N 2 activation .…”

Section: Introductionmentioning

confidence: 99%

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Non-Pincer-Type Arene Ru(II) Catalysts for the Direct Synthesis of Azines from Alcohols and Hydrazine under Aerobic Conditions

2020

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An efficient tandem synthetic approach to azines from the coupling of alcohols and hydrazine hydrate catalysed by newly synthesized arene Ru(II) complexes has been described. Two arene ruthenium(II) N-(pyrimidin-2-ylcarbamothioyl)furan-2carboxamide complexes have been fully characterised by analytical and spectral methods. The structures of the complexes have been confirmed with the aid of single-crystal X-ray analysis. The unprecedented coordination modes of N-(pyrimidin-2ylcarbamothioyl)furan-2-carboxamide ligand and the formation of four and six membered N,S-chelate complexes have been observed for the first time. Further, the new Ru(II) complexes act as an efficient catalyst for the synthesis of symmetrical azines. A diverse range of azines was synthesized. The products were isolated in good to excellent yields using a catalyst loading of 0.5 mol %. The catalytic reaction operates under aerobic and mild reaction conditions with the release of water as the only by-product. Plausible mechanism has been proposed and it is believed that the reaction proceeds initially via an aldehyde intermediate.

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Azines: synthesis, structure, electronic structure and their applications

Abstract: Azines (2,3-diaza-1,3-butadienes): structure, electronic structure, tautomerism, and their applications in organic synthesis, medicinal chemistry and materials chemistry.

Cited by 62 publications

References 238 publications

Synthesis, complete assignment of 1H- and 13C-NMR spectra and antioxidant activity of new azine derivative bearing coumarin moiety

Synthesis, complete assignment of 1H- and 13C-NMR spectra and antioxidant activity of new azine derivative bearing coumarin moiety

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

Non-Pincer-Type Arene Ru(II) Catalysts for the Direct Synthesis of Azines from Alcohols and Hydrazine under Aerobic Conditions

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