Synthesis of <i>N</i>‑Aryl and <i>N</i>‑Alkyl Phthalimidesvia Denitrogenative Cyanationof 1,2,3-Benzotriazin-4(3<i>H</i>)‑ones

An efficient metal-free approach for synthesizing <i>N</i>-aryl- and <i>N</i>-alkyl phthalimide derivatives from 1,2,3-benzotriazin-4(3<i>H</i>)-ones is described. The reaction likely proceeds via a denitrogenative cyanation pathway, utilizing TMSCN as the cyanide source. This method is straightforward as well as scalable and supports a wide range of substrates with high functional group tolerance, yielding diverse phthalimide derivatives in good to excellent yields. The utility of this method is further highlighted by the successful synthesis of a tyrosinase inhibitor analogue in good yield.

Publication Details

Journal
Figshare
Published
2025-02-21
DOI
https://doi.org/10.1021/acs.joc.4c02823.s001
Primary Topic
Technology, Environment, Urban Planning
Type
article
Field-Weighted Citation Impact
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article

Synthesis of N‑Aryl and N‑Alkyl Phthalimidesvia Denitrogenative Cyanationof 1,2,3-Benzotriazin-4(3H)‑ones

Figshare
Technology, Environment, Urban Planning
article

Synthesis of N‑Aryl and N‑Alkyl Phthalimidesvia Denitrogenative Cyanationof 1,2,3-Benzotriazin-4(3H)‑ones

article en

Abstract

An efficient metal-free approach for synthesizing <i>N</i>-aryl- and <i>N</i>-alkyl phthalimide derivatives from 1,2,3-benzotriazin-4(3<i>H</i>)-ones is described. The reaction likely proceeds via a denitrogenative cyanation pathway, utilizing TMSCN as the cyanide source. This method is straightforward as well as scalable and supports a wide range of substrates with high functional group tolerance, yielding diverse phthalimide derivatives in good to excellent yields. The utility of this method is further highlighted by the successful synthesis of a tyrosinase inhibitor analogue in good yield.

Figshare
Openalex Percentile: Top 56%
Technology, Environment, Urban Planning
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