Rhodium(II)‐Catalyzed [4+2] Annulation of Ester‐Tethered 1‐Sulfonyl‐1,2,3‐Triazoles and Hexahydro‐1,3,5‐Triazines

Duan, Shengguo; Meng, Huan; Jablasone, Saygbechi T.; Luo, Huan; Xu, Zefeng; Li, Chuan‐Ying

doi:10.1002/ajoc.202100098

Cited by 6 publications

(2 citation statements)

References 78 publications

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“…In order to explore the versatility of formaldehyde in the synthesis of other six-membered heterocycles, the reactions of N-benzyl-amine in the presence of formaldehyde and sodium hydrosulphide in different proportions were explored. The equimolar reaction between N-benzylamine and formaldehyde led exclusively to the formation of N-benzyltriazinane (3, 98% yield), which has already been previously reported by other research groups under different reaction conditions [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]. The reaction of one equivalent of Nbenzylamine with five of formaldehyde and three of sodium hydrosulphide was explored, obtaining a mixture of products in 50:50 ratios: N-benzyl-thiadiazinane (4) and Nbenzyl-dithiazinane (5).…”

Section: Versatility Of Formaldehyde In the Synthesis Of Six-member H...supporting

confidence: 53%

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: Versatility Of Formaldehyde In the Synthesis Of Six-member H...supporting

confidence: 53%

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

2023

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“…1,3,5-Triazinanes are a class of important synthetic building blocks and have been widely utilized in organic synthesis, especially as formaldimine precursors . They can be prepared from primary amines and formaldehyde easily and used as the precursors of unstable formaldimines . Their annulations with diazo compounds (including their precursors) were exploited and [1 + 2], [1 + 4] and [3 + 4], and [2 + 2 + 1] annulations were observed (Scheme a).…”

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confidence: 99%

Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines

Xie,

Wang,

2024

Org. Lett.

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Conversion of 1,3,5-triazinanes into 5-phosporyl-1,2,3,4tetrahydropyrimidines is achieved efficiently through the microwaveassisted reaction with phosphoryl diazomethanes. Both trialkyl and triaryl 1,3,5-triazinanes were converted by diazomethyldiarylphosphine oxides, dialkyl diazomethylphosphonates, and alkyl diazomethyl(aryl)phosphinates and functionalized simultaneously in good to excellent yields. The reaction is a sequence of 1,3,5-triazinane fragmentation, tandem nucleophilic addition of the generated formaldimines and phosphoryl diazomethanes, and final N,N-acetalization.

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Synthesis of 3‐Methylidene‐2,3‐dihydropyrroles via Formal 1,2‐Enamine Migration/Cyclization Cascade of Rhodium Carbenes

Jie

et al. 2023

Adv Synth Catal

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3‐Methylidene‐2,3‐dihydropyrroles with an ester or keto group at the C4 position were obtained in moderate to good yields from enamine‐tethered triazoles in the presence of a rhodium(II) catalyst. A formal 1,2‐enamine migration/cyclization cascade triggered by formation of an α‐amino carbene is proposed to illustrate the mechanism. The valuable exocyclic double bond showed distinctive reactivity, which is very useful for further introduction of functional groups. The dihydropyrrole is stable under neutral, weakly acidic, or weakly basic conditions.

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Rhodium(II)‐Catalyzed [4+2] Annulation of Ester‐Tethered 1‐Sulfonyl‐1,2,3‐Triazoles and Hexahydro‐1,3,5‐Triazines

Cited by 6 publications

References 78 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

Reaction of 1,3,5-Triazinanes with Phosphoryl Diazomethanes: Access to 5-Phosphoryl-1,2,3,4-tetrahydropyrimidines

Synthesis of 3‐Methylidene‐2,3‐dihydropyrroles via Formal 1,2‐Enamine Migration/Cyclization Cascade of Rhodium Carbenes

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