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Synthesis of julolidine derivatives via SnCl4-promoted spirocyclization of (1-alkyltetrahydroquinolin-8-yl) methylidene-1H-imidazol-5 (4H)-ones
Chemistry Of Heterocyclic Compounds. 2022. Vol. 58. P. 255–259.
Shirokova V., Smirnov A., Zaitseva E., Baleeva N., Mikhaylov A. A., Baranov M.
Voronin A., Sofya P. Balabanova, Fedyanin I. et al., Molecules 2022 Vol. 27 No. 19 Article 6287
A strategy for the synthesis of 5-((2-cyanoethyl)-X-amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides (X = H; CH2CH2CN; NO2 (4a); CN (4b); CO2Et (4c)) starting from 3-amino-4-azido-1,2,5-oxadiazole was developed. The key step in this strategy is the intramolecular thermolytic cyclization of the azido group and the bis(2-cyanoethyl)triazene group. Removal of the 2-cyanoethyl protecting group from amides 4a–c gave potassium salt of the corresponding nitramide and ...
Added: January 31, 2023
Ivanov D., Zaitseva E., Smirnov A. et al., Advanced Synthesis and Catalysis 2022 Vol. 364 No. 9 P. 1587–1595
Added: June 19, 2022
Larin A., Shaferov A., Kulikov A. et al., Chemistry - A European Journal 2021 Vol. 27 P. 14628–14637
cA series of novel energetic materials comprising of azo-bridged furoxanylazoles enriched with energetic functionalities was designed and synthesized. These high-energy materials were thoroughly characterized by IR and multinuclear NMR (1H, 13C, 14N) spectroscopy, high-resolution mass spectrometry, elemental analysis, and differential scanning calorimetry (DSC). The molecular structures of representative amino and azo oxadiazole assemblies were additionally confirmed by ...
Added: October 13, 2021
Belousov Y., Drozdov A., Taydakov I. et al., Coordination Chemistry Reviews 2021 Vol. 15 Article 214084
The unique optical and magnetic properties of lanthanide ions (Ln), like a gem, need the right faceting and the right setting. Azole carboxylic acids provide a unique platform for driving the structure of complex compounds ranging in dimensions from 0-D (molecular complexes) to 1-D, 2-D polymers and 3-D MOF (Metal Organic Framework) structures. The peculiarity ...
Added: October 4, 2021
Belyy A., Platonov D., Salikov R. et al., Dyes and Pigments 2021 Vol. 187 Article 109107
A novel class of fluorescent electron-deficient 5-hydroxyisoquinolones is proposed. The new luminophores are obtained via the reaction of stable and easily available hepta(methoxycarbonyl)cycloheptatrienyl potassium with alkylamines, anilines and acylhydrazines. The new one-pot protocol is efficient with a large scope of primary amines. The solvolysis of N-acylamino substituted 5-hydroxyisoquinolones and subsequent reactions have provided a pathway ...
Added: September 29, 2021
Nizovtsev A., Sokolov A., Smirnov A. et al., ChemistrySelect 2021 Vol. 6 No. 34 P. 8938–8941
Herein we report a short and general protocol for synthesis of potentially biologically active pyridine-2,6-diones. The approach is based on the redirection of the condensation of the intermediates of Dornow reaction – 5-hydroxy-1,2-oxazine-6-ones with primary amines by their prior O-alkylation. Such manipulation blocks their transformation into isoxazoles and allows one to obtain a library of 30+ ...
Added: September 9, 2021
Shirokova V., Ikonnikova V., Solyev P. et al., Synthesis 2021 Vol. 53 No. 24 P. 4689–4699
Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride shift-triggered cyclization to provide hardly accessible julolidine derivatives in 20-98% yield under scandium (III) triflate catalysis. The scope of the reaction, several follow-up transformations and a remarkable side-process discovered during the conditions optimization are highlighted. ...
Added: July 29, 2021
Ananyev I., Топчий М., Зотова М. et al., Chemistry - A European Journal 2017 Vol. 23 No. 27 P. 6663–6674
An efficient and scaled-up synthesis of the imidazol-2-ylidene-based unsymmetrical NHC precursors bearing the sterically demanding hexafluoroisopropylalkoxy group [(CF3)(2)(OR)C-] at the ortho position of the N-aryl substituent was developed. The key step of the method involved the transformation of a Mes-substituted oxazolinium tetrafluoroborate salt through the reaction with the corresponding binucleophilic fluoroalkyl-substituted aniline. The subsequent post-modification ...
Added: October 4, 2019
Ananyev I., Быстров Д., Жилин Е. et al., Advanced Synthesis and Catalysis 2018 Vol. 360 No. 16 P. 3157–3163
A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2-aminohetarene N-oxides was developed. The developed reaction is suitable for both five- and six-membered heterocycles and proceeds through the condensation of 2-aminohetarene N-oxide with trimethyl orthoformate followed by intramolecular N-oxide oxygen transfer. For five-membered hetarene N-oxides (furoxans), the intramolecular rearrangement is catalyzed by ...
Added: October 4, 2019
Ananyev I., Ларин А., Муравьев Н. et al., Chemistry - A European Journal 2019 Vol. 25 No. 16 P. 4225–4233
A series of highly energetic organic salts comprising a tetrazolylfuroxan anion, explosophoric azido or azo functionalities, and nitrogen-rich cations were synthesized by simple, efficient, and scalable chemical routes. These energetic materials were fully characterized by IR and multinuclear NMR (H-1, C-13, N-14, N-15) spectroscopy, elemental analysis, and differential scanning calorimetry (DSC). Additionally, the structure of ...
Added: October 4, 2019
Galenko E., Galenko A., Novikov M. et al., ChemistrySelect 2017 Vol. 2 No. 25 P. 7508–7513
New β‐diazopyrrole and β‐triazenylpyrrole derivatives were synthesized from isoxazoles and pyridinium salts in two and three steps, respectively. The apoptotic/necrotic difference for these compounds was estimated on THP‐1 cell line. The most effective of the panel is methyl 3‐diazo‐2‐(2,4‐dimethylphenyl)‐4‐phenyl‐3H‐pyrrole‐5‐carboxylate which demonstrated cytotoxic activity from the lowest concentration of 3.3 μM with a steep rise of the ...
Added: June 25, 2019