New dithiazinanes and bis‐dithiazinanes‐bearing pendant ethylamines: Structure and reactivity

Colorado‐Peralta, Raúl; López‐Rocha, Cristina A.; Sánchez-Ruíz, Sonia A.; Contreras, Rosalinda; Flores‐Parra, Angelina

doi:10.1002/hc.20657

Cited by 6 publications

(1 citation statement)

References 28 publications

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“…Condensation reactions between N-alkylethylenediamines, formaldehyde and sodium hydrosulphide in a stoichiometric ratio [1:5:3] led to the formation of N-alkyl-ethylenedithiazinanes, which were previously reported by our research group [24]. However, by varying stoichiometry, by-products were obtained, such as N-alkylethylenethiadiazinanes, or N-alkylethylenetriazinanes, which made it difficult to isolate pure compounds.…”

Section: Resultsmentioning

confidence: 99%

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

2023

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Formaldehyde is a simple chemical compound that is used as a building block in obtaining a wide range of products. The versatility of formaldehyde in chemical synthesis becomes evident when it is reacted with N-alkylethylenediamines. Therefore, this paper reports the structure and reactivity of a series of compounds derived from easily accessible molecules, such as formaldehyde, sodium hydrosulphide, and N-alkylethylenediamines. The 1,3,5-triazines (1a-1d) and bis(3-alkyl-imidazolidin-1-yl)methanes (2a-2d) were obtained by simple reaction conditions. Additionally, different proportions of sodium hydrosulphide and formaldehyde were used with N-benzylamine to obtain N-benzyltriazinane (3), N-benzylthiadiazinane (4) and N-benzyldithiazinane (5). All these compounds were characterized by analytical, spectroscopic, and spectrometric techniques, such as melting point, solubility, one-dimensional and two-dimensional nuclear magnetic resonance (13C, 1H, 15N, COSY, HETCOR, NOESY, COLOC), elemental analysis, high- and low-resolution mass spectrometry, among others. The structures of compounds 4 and 5 were obtained by single-crystal X-ray diffraction. The results show that small variations in the stoichiometry and the reaction conditions significantly influence the products obtained.

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Section: Resultsmentioning

confidence: 99%

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

2023

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Synthesis and Biological Evaluation of 1,3,5-Dithiazinanes: Synthesis, Stereochemistry and Applications

Akhmetova,

Akhmadiev

2024

S-Heterocycles

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Importance of p-block coordination chemistry with nitrogen- and sulphur-containing 1,3,5-heterocyclohexanes: Structural and dynamic behaviour involving weak interactions

Colorado-Peralta,

Flores-Parra

2024

Coordination Chemistry Reviews

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New dithiazinanes and bis‐dithiazinanes‐bearing pendant ethylamines: Structure and reactivity

Abstract: The structure and reactivity of a series of new ethylaminedithiazinanes and bis-diethylaminedithiazinanessynthesized from formaldehyde,

Cited by 6 publications

References 28 publications

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

Structural and Dynamic Behaviour of Heterocycles Derived from Ethylenediamines with Formaldehyde: 1,3,5-Triazinanes and Bis(imidazolidinyl)methanes

Synthesis and Biological Evaluation of 1,3,5-Dithiazinanes: Synthesis, Stereochemistry and Applications

Importance of p-block coordination chemistry with nitrogen- and sulphur-containing 1,3,5-heterocyclohexanes: Structural and dynamic behaviour involving weak interactions

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