Straightforward Three-Component Synthesis of N′,N′′-Disubstituted N-Alkyl-1,3,5-Triazinanes

Клецков, А. В.; Frontera, Antonio; Sinelshchikova, Anna А.; Grigoriev, Mikhail S.; Zaytsev, Vladimir P.; Grudova, Mariya V.; Bunev, Alexander S.; Presnukhina, Sofia I.; Shetnev, Аnton; Zubkov, Fedor I.

doi:10.1055/s-0039-1690900

Cited by 9 publications

(7 citation statements)

References 14 publications

(13 reference statements)

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“…This reaction worked indeed very well, the desired triazinanes were obtained in excellent yields (Scheme 2). This model of reaction is in agreement with the reported data in literature [18], and the CuFe 2 O 4 NPs shown potential catalytic activities more efficiently than Mg(ClO 4 ) 2 in the view of easily work-up, simple purification of desired products, high yield, mild reaction condition, and environmentally benign process.…”

Section: Scheme 1 Synthesis Of Compound 3asupporting

confidence: 91%

Study on the synthesis of 1,3,5-triazinane derivatives on copper-ferrite nanoparticles catalyst

Pham¹,

Pham²,

Cao

et al. 2021

IOP Conf. Ser.: Earth Environ. Sci.

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A high efficient method for the synthesis of 1,3,5-triaryltriazinane derivatives is developed by the condensation reaction of amines and formaldehyde followed by spontaneous cyclotrimerization using CuFe2O4 NPs as an environmentally benign catalyst at room temperature. The copper ferrite was easily separated, reused in good repetitive catalytic performance by simple filtration or external magnet. This process was efficient and compatible with wide range of amines to afford a direct access to nitrogen containing compounds in excellent yields up to 99% and high selectivity.

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Section: Scheme 1 Synthesis Of Compound 3asupporting

confidence: 91%

Study on the synthesis of 1,3,5-triazinane derivatives on copper-ferrite nanoparticles catalyst

Pham¹,

Pham²,

Cao

et al. 2021

IOP Conf. Ser.: Earth Environ. Sci.

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“…As it was mentioned above, the main objects of this work, N,N -disulfamide substituted triazinanes 1-4, were prepared according to the method described in our preliminary communication [12] using the three-component Mg(ClO 4 ) 2 catalyzed condensation of arylsulfonamides with paraformaldehyde and nor tert-butyl amine (Scheme 2, see the Supplementary Materials for detail of the experimental procedures and spectral data). The tert-butyland n-butylamines were chosen as the amino-components providing the highest yield of the target triazinanes.…”

Section: Methodsmentioning

confidence: 99%

Intramolecular sp2-sp3 Disequalization of Chemically Identical Sulfonamide Nitrogen Atoms: Single Crystal X-Ray Diffraction Characterization, Hirshfeld Surface Analysis and DFT Calculations of N-Substituted Hexahydro-1,3,5-Triazines

et al. 2020

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In this manuscript, the synthesis and single crystal X-ray diffraction characterization of four N-substituted 1,3,5-triazinanes are reported along with a detailed analysis of the noncovalent interactions observed in the solid state architecture to these compounds, focusing on C–H···π and C–H···O H-bonding interactions. These noncovalent contacts have been characterized energetically by using DFT calculations and also by Hirshfeld surface analysis. In addition, the supramolecular assemblies have been characterized using the quantum theory of “atoms-in-molecules” (QTAIM) and molecular electrostatic potential (MEP) calculations. The XRD analysis revealed a never before observed feature of the crystalline structure of some molecules: symmetrically substituted 1,3,5-triazacyclohexanes possess two chemically identical sulfonamide nitrogen atoms in different sp2 and sp3-hybridizations.

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“…Moreover, the catalytic asymmetric variants of the above-mentioned aminomethylations and cyclizations of 1,3,5-triazinanes are still in their infancies. Considering the growing field of catalysis 36,37 and development of new synthetic methods for 1,3,5-triazinane synthesis, 38 it is believed that additional new and useful 1,3,5-triazinane chemistry will be discovered in the near future.…”

Section: Liang Et Almentioning

confidence: 99%

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Liang¹,

Xiao²,

Chen³

2020

Synthesis

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1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.1 Introduction2 Aminomethylations with 1,3,5-Triazinanes3 Cycloadditions with 1,3,5-Triazinanes3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons4 Conclusions

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Straightforward Three-Component Synthesis of N′,N′′-Disubstituted N-Alkyl-1,3,5-Triazinanes

Cited by 9 publications

References 14 publications

Study on the synthesis of 1,3,5-triazinane derivatives on copper-ferrite nanoparticles catalyst

Study on the synthesis of 1,3,5-triazinane derivatives on copper-ferrite nanoparticles catalyst

Intramolecular sp2-sp3 Disequalization of Chemically Identical Sulfonamide Nitrogen Atoms: Single Crystal X-Ray Diffraction Characterization, Hirshfeld Surface Analysis and DFT Calculations of N-Substituted Hexahydro-1,3,5-Triazines

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

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