Rational synthetic methods in creating promising (hetero)aromatic molecules and materials

Zyryanov, Grigory V.; Kopchuk, Dmitry S.; Коvalev, Igor S.; Rahman, Matiur; Khasanov, Albert F.; Krinochkin, Alexey P.; Taniya, Olga S.; Чупахин, О. Н.; Charushin, Valery N.

doi:10.1016/j.mencom.2020.09.001

Cited by 18 publications

(5 citation statements)

References 219 publications

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“…As easy as 2012, Amanpour and co-workers [84] furnished an efficient and simple approach for the synthesis of biologically interesting phenazine derivatives (51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64). As shown in Scheme 9, 14 highly functionalized phenazine derivatives (51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64) were selectively achieved by the one-pot, four-component condensation reaction and were gotten good to excellent yields in the absence of any catalysts in N, N-dimethlformamide. Additionally, this approach also allowed for the synthesis of expected products due to simple and readily available precursors under neutral conditions without activation or modifications.…”

Section: Benzo[a]pyrano[23-c]phenazine and Derivativesmentioning

confidence: 99%

“…In sharp contrast, these synthetic strategies epitomize powerful alternatives with sustainable, facile, and highefficient principles for the formation of complex molecules, such as electrochemical strategy, biosynthesis, microwave method, supramolecular catalysis, photocatalysis, and some chemical synthesis [16,[44][45][46][47][48][49][50][51][52][53][54][55][56]. Notably, these strategies effectively avoid the major drawbacks of traditional methods and simultaneously provide concise process to furnish structurally various phenazine derivatives in good to excellent yields [49,[57][58][59][60][61][62][63].…”

Section: Introductionmentioning

confidence: 99%

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Synthetic strategies of phenazine derivatives: A review

Che

et al. 2022

Journal of Heterocyclic Chem

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Since the growing importance of phenazine derivatives, the efficient synthetic strategies for the preparation of phenazine derivatives have attracted great attention from organic methodology. Herein, we comprehensively review and summarize a series of sustainable and facile synthetic strategies of phenazine derivatives. Moreover, we further discuss the approach of preparation and the superiority of each strategy.

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Section: Benzo[a]pyrano[23-c]phenazine and Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic strategies of phenazine derivatives: A review

Che

et al. 2022

Journal of Heterocyclic Chem

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“…[ 27 ] Hydrogen atoms are located in different Fourier diagrams. [ 28 ] Table 1 shows the crystal structure data of the three complexes.…”

Section: Experimentamentioning

confidence: 99%

Three novel spiral chain Nd (III) Eu (III) Sm (III)complexes bridged by 1,1 '(1,4‐phenylene‐bis [methylene])‐bis (pyridine‐3‐carboxylicaicd): Synthesis, structural characterization, and antitumor activity

Liu

et al. 2021

Applied Organom Chemis

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In this work, three new complexes [Ln2(L)3·H2O]n (where Ln = Nd(1)、Eu (2) and Sm (3)) have been synthesized by H2L (H2L = 1,1 ‘(1,4‐phenylene‐ bis [methylene])‐bis (pyridine‐3‐carboxylicaicd)) and were characterized by X‐ray single crystal diffraction and PXRD. The interaction of these complexes with FS DNA (fish sperm DNA) and the DNA binding constants of the complexes were determined using UV spectroscopy, indicating their ability to bind to FS DNA. The DNA binding constants k of the three complexes were 1.0186 × 104, 5.047 × 103, and 5.115 × 103, respectively. The results of UV spectrum showed that the complex 1–3 was bound to DNA through hydrogen bonding. The interaction of the complexes with FS DNA was studied by fluorescence spectroscopy. The stern‐volmer quenching values of complexes 1, 2, and 3 were 0.186, 0.093, and 0.114, respectively. Electrophoresis experiments showed that the three complexes could cleave DNA molecules. In addition, flow cytometry, and morphological apoptosis studies showed that the complex could induce apoptosis of HeLa tumor cells. Results all the three complexes had potential medicinal value.

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“…For example, carbonyl compounds were studied in the reaction of diamine addition and in the synthesis of azomethines, which were involved in the nitroaldol reaction. A rational method for the preparation of imidazo [1,2-a]pyridines can be obtained through the binucleophilic addition of 2-aminopyridines to nitroalkenes [6]. The addition of various reagents to the double bond of substituted ethylenes has been studied in the following reactions.…”

Section: Introductionmentioning

confidence: 99%

Theoretical evaluation of phenyl-substituted aziridines, azirines and epoxides reactivity

Borodina,

Novikov,

Zyryanov

et al. 2023

Chem

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The reactivity of three-membered heterocycles such as phenyl-substituted aziridines, azirines, epoxides was studied in comparison with styrenes, azomethines and carbonyl com-pounds which are most often used in organic synthesis in nucleophilic and electrophilic reactions. In accordance with electronic reactivity indices of nucleophilicity and electrophilicity calculated on the base of DFT approach, the substituted molecules of azirines, aziridines, and epoxides ex-hibit the similar reactivity to aldehydes and styrenes. In all cases, our predictions were checked against the experimental observations given in literature. All considered compounds mainly characterizes by the properties of medium-strength electrophiles. Aziridines, azirines, epoxides with two aryl groups show the best electrophilic properties. This observation can be used in predictions of reactivity for these classes of compounds. Among three-membered heterocycles, the best nucleophilic properties were observed for substituted epoxy cycles. We have found that the dual descriptor based on Fukui functions cannot be recommended for predictions the reactivity of aziridines and epoxides. The values of the dual descriptor on both carbon atoms in three-membered ring significantly differ, while the experimental data on nucleophilic addition indicate that the reaction proceeds at both carbon atoms. Nevertheless, for phenyl-substituted azirines, the descriptor based on Fukui functions shows its effectiveness quite well.

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Rational synthetic methods in creating promising (hetero)aromatic molecules and materials

Cited by 18 publications

References 219 publications

Synthetic strategies of phenazine derivatives: A review

Synthetic strategies of phenazine derivatives: A review

Three novel spiral chain Nd (III) Eu (III) Sm (III)complexes bridged by 1,1 '(1,4‐phenylene‐bis [methylene])‐bis (pyridine‐3‐carboxylicaicd): Synthesis, structural characterization, and antitumor activity

Theoretical evaluation of phenyl-substituted aziridines, azirines and epoxides reactivity

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