Molecular rearrangements of 4‐iminomethyl‐1,2,3‐triazoles. Replacement of 1‐aryl substituents in 1<i>H</i>‐1,2,3‐triazole‐4‐carbaldehydes

L'abbé, G.; Bruynseels, Maria; Delbeke, Pieter; Toppet, Suzanne

doi:10.1002/jhet.5570270733

Cited by 39 publications

(21 citation statements)

References 24 publications

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“…The reagent is easily prepared from a variety of synthetically accessible azide compounds and 3,3‐diethoxyprop‐1‐yne by copper‐catalyzed azide–alkyne cycloaddition (CuAAC) . Furthermore, it is found that a primary amine compound containing a functional molecule can be converted into a TA4C reagent through a unique Dimroth rearrangement . This reaction scheme represents the simplest process developed thus far for preparing N‐terminal modified proteins using a TA4C derivative (Figure B).…”

Section: Figurementioning

confidence: 99%

“…Next, to explore a facile process for generation of TA4C reagents, we focused on a Dimroth rearrangement reaction via a ring‐degenerate rearrangement of 1‐substituted 1,2,3‐triazole‐4‐carbaldehyde (Figure ) . In this process, the primary amine was found to be incorporated into the triazole moiety when 1‐(4‐nitrophenyl)‐1 H ‐1,2,3‐triazole‐4‐carbaldehyde ( 13 ) with an electron‐withdrawing 4‐nitrophenyl group is used .…”

Section: Figurementioning

confidence: 99%

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Triazolecarbaldehyde Reagents for One‐Step N‐Terminal Protein Modification

et al. 2020

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Site-specific modification of peptides and proteins is ak ey aspect of protein engineering.W ed eveloped am ethod for modification of the Nterminus of proteins using 1H-1,2,3-triazole-4-carbaldehyde( TA4C) derivatives, which can be prepared in one step. The N-terminal specific labelingo fb ioactive peptides and proteins with the TA4C derivatives proceeds under mild reactionc onditions in excellent conversion (angiotensinI: 92 %, ribonuclease A: 90 %). This method enables site-specific conjugation of various functional molecules such as fluorophores,b iotin, and polyethylene glycol attached to the triazole ring to the Nterminus. Furthermore, af unctional molecule modified with ap rimary amine moiety can be directly converted into aT A4C derivativethrough aDimroth rearrangement reaction with 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde. This methodc an be used to obtain N-terminal-modifiedp roteins via only two steps:1 )convenient preparation of aT A4C derivativew ith af unctional group and 2) modification of the Nterminus of the protein with the TA4C derivative.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Triazolecarbaldehyde Reagents for One‐Step N‐Terminal Protein Modification

et al. 2020

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“…Recentemente, Fabian e Bakulev 42 utilizando cálculos teóricos confirmaram a proposta de que ocorre uma ciclização pseudopericíclica. Muitos outros trabalhos mostraram que este rearranjo também ocorre em triazóis contendo os substituintes diazometil 43 , amino [43][44][45] . Utilizando-se este método, α-formildiazoésteres foram aplicados na síntese de antibióticos triazólicos 53 e de novos possíveis intermediários para sua obtenção 54 .…”

Section: Metodologia Via Ciclização [2n + 1n]unclassified

Heterociclos 1,2,3-triazólicos: histórico, métodos de preparação, aplicações e atividades farmacológicas

Melo¹,

Donnici²,

Augusti³

et al. 2006

Quím. Nova

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Recebido em 7/4/05; aceito em 21/7/05; publicado na web em 16/2/06 1,2,3-TRIAZOLIC HETEROCYCLES: HISTORY, PREPARATIONS, APPLICATIONS AND PHARMACOLOGICAL ACTIVITIES. The 1,2,3-triazole, known since the end of 19 th century, is a very widely used heterocyclic system present in many synthetic substances and commercial pharmaceutical compounds. In fact, 1,2,3-triazoles show several applications in many areas especially as medicines against many diseases like cancer, AIDS, Parkinson and Alzheimer. Nowadays there is a large variety of known methods to obtain these heterocyclic compounds comprising mainly three synthetic routes. Nevertheless, there is no article that gives an objective overview of the synthetic methods for obtaining these kinds of azoheterocycles. This paper presents a brief history of this class of compounds, and a synthetic discussion concerning the main synthetic methods for its preparation, such as cyclization through hydrazones, concerted cycloadditon [2+3] and pseudopericyclic cyclization -and some others of restricted application, but also important. Finally, this paper also provides a brief overview on pharmacological applications of some 1,2,3-triazoles.

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“…DMSO was selected as the reaction solvent for these studies due to its proven utility in facilitating this reaction [42] and its low volatility. A reaction temperature of 100 °C was identified as useful for promoting significant reaction progress within a 24 h time window for the amine reactants studied.…”

Section: Resultsmentioning

confidence: 99%

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

Fletcher¹,

Hanson²,

Christensen³

et al. 2018

Beilstein J. Org. Chem.

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The 1-substituted-4-imino-1,2,3-triazole motif is an established component of coordination compounds and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing the ring-degenerate rearrangement reactions of 1-substituted-4-imino-1,2,3-triazoles, expanding on trends first observed by L’abbé et al. The efficiency of condensation between 4-formyltriazole and amine reactants as well as the propensity of imine products towards rearrangement was each strongly influenced by the substituent identity. It was observed that unsymmetrical condensation reactions conducted at 70 °C produced up to four imine products via a dynamic equilibrium of condensation, rearrangement and hydrolysis steps. Kinetic studies utilizing 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde with varying amines showed rearrangement rates sensitive to both steric and electronic factors. Such measurements were facilitated by a high throughput colorimetric assay to directly monitor the generation of a 4-nitroaniline byproduct.

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Molecular rearrangements of 4‐iminomethyl‐1,2,3‐triazoles. Replacement of 1‐aryl substituents in 1H‐1,2,3‐triazole‐4‐carbaldehydes

Cited by 39 publications

References 24 publications

Triazolecarbaldehyde Reagents for One‐Step N‐Terminal Protein Modification

Triazolecarbaldehyde Reagents for One‐Step N‐Terminal Protein Modification

Heterociclos 1,2,3-triazólicos: histórico, métodos de preparação, aplicações e atividades farmacológicas

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

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