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N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights.

ABSTRACT: A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol ? o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2 H-indazole synthesis, its reactivity was modulated for indazolone formation.

SUBMITTER: Zhu JS

PROVIDER: S-EPMC6451655 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights.

Zhu Jie S JS Kraemer Niklas N Shatskikh Marina E ME Li Clarabella J CJ Son Jung-Ho JH Haddadin Makhluf J MJ Tantillo Dean J DJ Kurth Mark J MJ

Organic letters 20180801 16

A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2 H-indazole synthesis, its reactivity was modulated for indazolone formation. ...[more]

PMID: 30067041

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