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CC BY 4.0 · SynOpen 2023; 07(03): 430-465
DOI: 10.1055/a-2157-5782
DOI: 10.1055/a-2157-5782
review
Synthetic Utility of N-Acylbenzotriazoles
The authors sincerely thank the Science Engineering and Research Board (SERB), New Delhi (Grant No. CRG/2021/002776) and Council of Scientific & Industrial Research (CSIR), New Delhi (Scheme No.: 02/(0345)/19/EMR-II) for the funding and Institute of Eminence (IoE) Banaras Hindu University BHU for the incentive grant. M.S.Y. gratefully acknowledges CSIR for the Senior Research Fellowship (CSIR).
Abstract
N-Acylbenzotriazoles are valuable synthons in organic synthesis. They are particularly used as acylating agents and an alternative to acyl chlorides. They have been widely explored for a diverse range of applications. This review summarizes methods for the preparation of N-acylbenzotriazole derivatives and their diverse applications, in particular demonstrating their ability 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.
1 Introduction
2 Synthesis of N-Acylbenzotriazoles
3 Applications of N-Acylbenzotriazoles in Organic Synthesis
3.1 N-Acylation Using N-Acylbenzotriazoles
3.2 C-Acylation of Heterocycles Using N-Acylbenzotriazoles
3.3 Preparation of β-Keto Esters and β-Diketones by Acylative Deacetylation
3.4 N-Acylbenzotriazoles Used for the Preparation of Other Valuable Intermediates
3.5 Benzotriazole Ring Cleavage (BtRC) Reactions
4 N-Acylbenzotriazoles as Catalysts and Ligands
5 Pharmacological Applications of N-Acylbenzotriazoles
6 Conclusions and Future Outlook
Key words
N-acylbenzotriazole - acylation - denitrogenative ring cleavage - acylative deacetylation - benzotriazole ring cleavage reactionsPublikationsverlauf
Eingereicht: 14. Mai 2023
Angenommen nach Revision: 16. August 2023
Accepted Manuscript online:
21. August 2023
Artikel online veröffentlicht:
27. September 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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