A simple and versatile method to synthesize N-acyl-benzotriazoles

Laconde, Guillaume; Amblard, Muriel; Martinez, Jean

doi:10.1016/j.tetlet.2018.12.046

Cited by 11 publications

(6 citation statements)

References 29 publications

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“…In addition, T3P was used for the synthesis of biotin and N -Fmoc polyethylene glycol derivatives. 18…”

Section: Synthesis Of N -Acylbenzotriazolesmentioning

confidence: 99%

Synthetic Utility of N-Acylbenzotriazoles

Tiwari,

Yadav,

Gupta

et al. 2023

SynOpen

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N-Acylbenzotriazoles are valuable synthons in organic synthesis. They are particularly used as acylating agents and an alternative to acyl chloride. They have been widely explored for a diverse range of applications. This review summarizes the methods for the preparation of N-acylbenzotriazole derivatives and their diverse applications in particular demonstration to serve as alternative acylating agents in organic transformations such as N-, O-, C-, and S-acylating agents for the convenient synthesis of a wide range of biologically important organic compounds. We also emphasize the synthesis of diverse compounds using benzotriazole ring cleavage (BtRC) methodology, including its pharmacophore study and some notable utilities as valuable starting materials, ligands, and intermediates in the field of organic synthesis.

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“…In addition, T3P was used for the synthesis of biotin and N -Fmoc polyethylene glycol derivatives. 18…”

Section: Synthesis Of N -Acylbenzotriazolesmentioning

confidence: 99%

Synthetic Utility of N-Acylbenzotriazoles

Tiwari,

Yadav,

Gupta

et al. 2023

SynOpen

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“…Thus, to facilitate their prepartion, some specific sets of reagents are thionyl chloride (3-4 equiv. ), 29 1-(methane sulfonyl chloride) with Et3N, 10 I2/PPh3 or NBS/PPh3 or, TCT/PPh3 or, PyS-SPy/PPh3 or, TClCA/PPh3 or, CCl3CN or, T3P® with or without base, [30][31][32][33][34][35][36][37] tosyl chloride with base, 38 EDC or DCC, 39 and acetonitrile/CDI 40 (Figure 1). However, these reactants have multiple disadvantages including significant toxicity in some cases, external base usage, and poor yields.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-acylbenzotriazole using acid anhydride

singh¹,

Pandey²,

Prajapati³

et al. 2022

Arkivoc

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A novel approach has been adopted for the conversion of carboxylic acids into corresponding N-acyl benzotriazoles utilizing acid anhydride. Our trial has ascertained 2,2,2-trifluoroacetic anhydride in anhydrous dichloromethane as the best candidate to achieve the targeted goal. The reliable and reproducible outcomes of the developed method are easy handling, wide substrate scope, and one-pot high-yielding under mild reaction condition. Moreover, the elimination of external base usage makes this procedure of utmost advantage in Nacyl benzotriazole synthesis.

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“…The reaction was carried out in the presence of N-propanephosphonic acid anhydride (T3P), in a mixture of pyridine/DMF, at room temperature. [18]…”

Section: Introductionmentioning

confidence: 99%

Unexpected Reactivity of N‐Acyl‐Benzotriazoles with Aromatic Amines in Acidic Medium (ABAA Reaction)

2018

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Despite the large number of methods for the synthesis of amides, formation of the amide bond from aromatic amines has always been a challenge for organic chemists due to their weak nucleophile character. We describe here a new efficient method of amide formation from N‐Acyl‐Benzotriazoles and Aromatic Amines (ABAA reaction) including aniline derivatives, in acidic conditions. This reaction is selective for aromatic amines, since aliphatic amines did not react under the same experimental conditions. Using the ABAA reaction, we have synthesized a series of aromatic amide compounds including labelled enzyme substrates, in excellent yield. The ABAA reaction also allowed the one‐pot synthesis of Nordiazepam, which is a precursor of the anxiolytic Diazepam (Valium®). This procedure opens new ways of synthesis of amides from aromatic amines, as well as of heterocyclic structures.

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A simple and versatile method to synthesize N-acyl-benzotriazoles

Cited by 11 publications

References 29 publications

Synthetic Utility of N-Acylbenzotriazoles

Synthetic Utility of N-Acylbenzotriazoles

Synthesis of N-acylbenzotriazole using acid anhydride

Unexpected Reactivity of N‐Acyl‐Benzotriazoles with Aromatic Amines in Acidic Medium (ABAA Reaction)

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