Behavior of acylated 1-hydroxybenzotriazole

Horiki, Kusuo

doi:10.1016/s0040-4039(01)83635-2

Cited by 24 publications

(16 citation statements)

References 5 publications

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“…The N -hydroxy form has been crystallized from water-free EtOH/Et 2 O after drying the compound over P 2 O 5 at 50 °C, whereas the N -oxide form was obtained from MeOH/H 2 O. [32] Also, acylation of BtOH can produce O - or N -acylation, depending upon the polarity of the reaction medium, [33–35] and the O -acyl compound completely isomerizes to the N -acyl form in the solid state. [35] …”

Section: Resultsmentioning

confidence: 99%

“…[23–25] In a Cu(OAc) 2 -catalyzed method, 1 H -benzotriazole underwent reaction with substituted thiophenes, furans, and pyrroles, in the presence of Selectfluor. [26] N -(2-Hydroxyaryl)benzotriazoles have been prepared by O -arylation with diaryliodonium triflates, followed by a [33] sigmatropic rearrangement. [27] A summary of these methods is shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

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The Disappearing Director: The Case of Directed N‐Arylation via a Removable Hydroxyl Group

et al. 2018

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A facile and broadly applicable method for the regiospecific N-arylation of benzotriazoles is reported. Copper-mediated reactions of diverse 1-hydroxy-1H-benzotriazoles with aryl boronic acids lead to 1-aryl-1H-benzotriazole 3-oxides. A N1-OH → N3 prototropy in the 1-hydroxy-1H-benzotriazoles is plausibly the underlying basis, where the tautomer is captured by the boronic acid, leading to C–N (not C–O) bond formation. Because the N–O bond in amine N-oxides and 1-hydroxy-1H-benzotriazoles can be easily reduced by diboron reagents such as (pinB)2 and B2(OH)4, exposure of the 1-aryl-1H-benzotriazole 3-oxides to B2(OH)4 then leads to facile reduction of the N–O bond resulting in diverse, regiospecifically-arylated benzotriazoles. Thus, the N-hydroxyl group in 1-hydroxy-1H-benzotriazoles acts as a disposable arylation director.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Disappearing Director: The Case of Directed N‐Arylation via a Removable Hydroxyl Group

et al. 2018

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“…We investigated the IDP with acetamide groups. Although N-terminal selective acetylation using acetic anhydride has been reported by Noga et al [15], 1-acetoxybenzotriazol and 1-deutrioacetoxybenzotriazole were chosen as the labeling reagents [16,17]. These are readily preparable, inexpensive, not volatile, stable for storage, easy to handle because it's in powder form, and reactive enough for acetamide formation reactions.…”

Section: Applications With Isotopic Acetamides At the N-terminusmentioning

confidence: 99%

Isotopic Differentiation Protocol, a Selective Extraction of C- and N-Terminal Ions in ESI-Ms/Ms De Novo Peptide Sequencing

Fujii¹,

Chiba²,

Tamayama³

et al. 2015

Nat Prod Chem Res 2015

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Simple and selective extraction method of C-and N-terminal ions in ESI-MS/MS analyses, named isotopic differentiation protocol (IDP), was developed. It takes advantage of the mass-difference between the isotopologues after methyl and deuterated methyl ester formations at the C-terminal carboxylic acid or acetamide and deuterated acetamide formations at the N-terminal amines. This method distinguishes the N-terminal and C-terminal ions in principle to facilitate the de novo peptide sequencing. An application with non-ribosomal depsipeptide plipastatin revealed that a pair of the peptide and the corresponding methyl ester at the C-terminus was also applicable to IDP method giving spectrum with enough quality. Facilitating software named "MSMS Search Tool" was also developed.

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“…These types of active ester can suppress epimerization. N-Hydroxybenzotriazole (HOBt) ester 101 can be easily prepared by the DCC method, it suppresses epimerization and accelerated aminolysis, and therefore it is widely used in peptide synthesis [241,242]. The HOSu ester is easily prepared from the N-protected amino acid and HOSu with DCC.…”

Section: Active Estersmentioning

confidence: 99%