Refernces
10.1016/j.cclet.2013.11.024
The research presented in the scholarly article focuses on the development of a highly selective two-photon fluorescent probe, ADNO (2-(α-(3,4-diaminophenoxy)acetyl)-6(dimethylamino)naphthalene), for imaging nitric oxide (NO) in living cells. The probe is designed based on the photoinduced electron transfer (PET) mechanism, utilizing o-phenylenediamine as the NO-sensitive fluorescence modulator and 2-acetyl-6-(dimethylamino)naphthalene (Acedan) as the two-photon fluorophore. The detection of NO is achieved by monitoring the alteration of electron-donating capacity of the o-phenylenediamine moiety, which quenches the fluorescence of Acedan but is reversed in the presence of NO due to the transformation into benzotriazole, thus reviving fluorescence. The probe's rapid response, remarkable fluorescent enhancement, and excellent chemoselectivity for NO over other reactive oxygen/nitrogen species (ROS/RNS) and common metal ions were demonstrated through a series of experiments. These experiments included the synthesis of ADNO, its spectral characterization, and its application in fluorescence imaging of NO in living cells using both one-photon microscopy (OPM) and two-photon microscopy (TPM). The study also assessed the probe's performance at various pH levels and its stability and selectivity in the presence of different ROS/RNS and metal ions. The research utilized various analytical techniques such as NMR, mass spectrometry, UV–vis, and fluorescence spectroscopy to characterize the probe and evaluate its performance.
10.1007/s11172-008-0063-2
The research focuses on the synthesis and study of benzotriazolylsuccinimides, which are based on benzotriazole (Bt) and maleimides. The experiments involved the condensation of Bt with N-phenylmaleimide (PMI) in a melt at temperatures ranging from 120 to 220 °C. The reaction was conducted in a fluoroplast cup to prevent side reactions such as homopolymerization of maleimides. The products were analyzed using 1H and 13C NMR spectroscopy, which confirmed the formation of both (benzotriazol-1-yl) and (benzotriazol-2-yl)succinimides, with the latter being a minor product. Fourier-transform IR spectroscopy was also used to record the spectra of the synthesized compounds. The reactants included Bt, PMI, and various bismaleimides such as N,N'-hexamethylenebimaleimide (HMBMI), N,N'-methylene(4,4'-diphenyl)bimaleimide (MDPBMI), and N,N'-oxido(4,4'-diphenyl)bimaleimide (ODPBMI). The analyses showed that the reaction could proceed through two paths, leading to the formation of both types of succinimides, and also indicated the presence of residual maleimide fragments, suggesting the reaction was not complete under the studied conditions.
10.1016/j.tetlet.2008.06.110
The research focuses on the development of a new method for synthesizing MBHA (4-methylbenzhydrylamine) resin, a widely used solid support for the synthesis of carboxamides or peptide C-terminal amides. The study introduces a benzotriazole-mediated amidoalkylation approach to prepare MBHA resin, utilizing N-[(benzotriazol-1yl)(p-tolyl)methyl]formamide or N-[formamido(p-tolyl)methyl]formamide as key reactants. The experiments involved the reaction of these compounds with benzene in the presence of aluminum chloride to achieve the amidoalkylation of unactivated aromatic compounds like benzene. The resulting products were then subjected to hydrolysis to obtain the MBHA resin, which was characterized by its loading capacity determined through Fmoc titration after coupling with Fmoc-Gly-OH. The resin's performance was evaluated by synthesizing a model peptide, Leu-enkephalin, and analyzing the crude product using HPLC and MALDI-TOF. The study demonstrated that the benzotriazole-mediated amidoalkylation method is effective for synthesizing MBHA resin with high loading capacity and good properties as a solid support for solid-phase peptide synthesis (SPPS).
10.1016/j.inoche.2008.05.023
The research aimed to develop a new microwave-assisted synthesis methodology for the preparation of ferrocene amides, which are derivatives of ferrocene with widespread applications in chemistry. The study utilized a direct 1H-Benzotriazole/SOCl2 methodology to derivatize ferrocene carboxylic acid, creating N-ferrocenoyl benzotriazole as a novel starting material for the functionalization of the ferrocene ring. This compound was then reacted with mono- and di-amines under microwave irradiation to synthesize ferrocene mono- and di-amides in high purity and good yield. The researchers concluded that microwave synthesis offers advantages in terms of reaction time and product yield compared to conventional methods, and their approach using N-ferrocenoyl benzotriazole as a starting material is a new, easy, and fast synthetic method for the preparation of ferrocene amides. The chemicals used in the process included ferrocene carboxylic acid, 1H-benzotriazole, thionyl chloride (SOCl2), and various amines such as ammonium hydroxide, cyclohexylamine, piperidine, morpholine, and others listed in Table 1 of the article.
10.1002/ejoc.202001543
The research presents a metal-free method for synthesizing benzotriazoles using a flow reactor. The key chemicals involved in this process include azides and arynes, which undergo a [3+2] cycloaddition reaction to form benzotriazoles. The researchers optimized the reaction conditions, using tetrabutylammonium triphenyldifluorosilicate (TBAT) as a fluoride source and acetonitrile as the solvent, achieving high yields and scalability. The study demonstrates the synthesis of various benzotriazoles with different substitution patterns, highlighting the potential for rapid and safe production of these compounds, which have applications in medicinal chemistry and bioorthogonal chemistry.
10.3184/030823407X272985
The study presents a straightforward and racemisation-free method for synthesizing N-urethane protected β-amino alcohols and peptidyl alcohols through the reduction of N-(protected-α-aminoacyl)benzotriazoles using sodium borohydride (NaBH4). The N-protected amino alcohols and peptidyl alcohols are significant synthetic intermediates, widely used in the synthesis of various compounds with diverse synthetic and biological applications. The researchers reacted amino acids or peptide acids with benzotriazole pretreated with SOCl2 to produce N-protected amino acylbenzotriazoles, which were then reduced to the corresponding alcohols by NaBH4 in methanol at room temperature. The method is practical, fast, and efficient, yielding high-purity alcohols in excellent yields (95–99%). The study also demonstrated that common side chain protecting groups remained unaffected during the reduction process.
10.1055/s-0030-1259988
The research aims to develop a simple and practical protocol for reducing carboxylic acids to alcohols using hydroxybenzotriazole esters as intermediates. The study explores the use of 1-hydroxybenzotriazole (HOBt) and carbodiimide (EDC) to form these reactive intermediates, which are then reduced by sodium borohydride in the presence of water. The researchers found that the reaction proceeds with excellent yields and tolerates various functional groups, including methoxy, phenoxy, and nitro groups. The protocol was successfully applied to a wide range of carboxylic acids, including phenylacetic acids, benzoic acids, and amino acids, yielding the corresponding alcohols in high yields. The study concludes that this method provides a general, rapid, and convenient approach for the reduction of carboxylic acids, making it a useful tool for selective reduction in the synthesis of complex molecules.
10.1007/s10593-008-0093-6
The study focused on the reaction of phenyl glycidyl ether with various heterocyclic compounds to synthesize new compounds with potential biological activity. The chemicals used included 5,5-dimethylhydantoin, morpholine, benzotriazole, benzimidazole, pyrrolidone, phthalimide, and 8-hydroxyquinoline. These heterocyclic compounds served as reactants to form N-(2-hydroxy-3-phenoxypropyl) derivatives, which are of interest due to their potential to contain pharmacophoric fragments that could lead to the discovery of new biologically active substances. The purpose of the study was to develop a one-stage method for synthesizing these derivatives, which could be applied in preparative chemistry and contribute to the development of new drugs.
10.1139/v80-010
The study investigates the preparation, characterization, and reactions of N-tert-butyldimethylsilyl derivatives of various heterocyclic compounds, including imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, 1,2,4-triazole, and benzotriazole. These derivatives were synthesized using tert-butyldimethylsilyl chloride and the corresponding heterocyclic compounds. The products were identified and characterized using carbon and proton nuclear magnetic resonance (NMR), mass spectrometry, and elemental analysis. The study confirmed the absence of intermolecular silyl exchange at ambient temperature through carbon NMR spectra, but noted that such exchange occurred at elevated temperatures (130-160°C). The study also explored the reaction of these silyl derivatives with dimethylsulfoxide (DMSO), resulting in the formation of N-(methylthio)methyl derivatives of the heterocycles. The mechanism for this reaction involves a Pummerer rearrangement, and the products were characterized using various analytical techniques, providing insights into the stability and reactivity of these compounds under different conditions.
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