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MnO2-Mediated Oxidative Cyclization of "Formal" Schiff's Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines.

ABSTRACT: A different type of MnO2-induced oxidative cyclization of dihydrotriazines has been developed. These dihydrotriazines are considered as a "formal" Schiff's base. This method provided easy access to naphthofuro-fused triazine via the C-C/C-O oxidative coupling reaction. The reaction sequence comprised the nucleophilic addition of 2-naphthol or phenol to 1,2,4-triazine, followed by oxidative cyclization. The scope and limitations of this novel coupling reaction have been investigated. Further application of the synthesized compound has been demonstrated by synthesizing carbazole-substituted benzofuro-fused triazines. The scalability of the reaction was demonstrated at a 40 mmol load. The mechanistic study strongly suggests that this reaction proceeds through the formation of an O-coordinated manganese complex.

SUBMITTER: Fatykhov RF 

PROVIDER: S-EPMC9611995 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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MnO<sub>2</sub>-Mediated Oxidative Cyclization of "Formal" Schiff's Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines.

Fatykhov Ramil F RF   Khalymbadzha Igor A IA   Sharapov Ainur D AD   Potapova Anastasia P AP   Mochulskaya Nataliya N NN   Tsmokalyuk Anton N AN   Ivoilova Alexandra V AV   Mozharovskaia Polina N PN   Santra Sougata S   Chupakhin Oleg N ON  

Molecules (Basel, Switzerland) 20221021 20

A different type of MnO<sub>2</sub>-induced oxidative cyclization of dihydrotriazines has been developed. These dihydrotriazines are considered as a "formal" Schiff's base. This method provided easy access to naphthofuro-fused triazine via the C-C/C-O oxidative coupling reaction. The reaction sequence comprised the nucleophilic addition of 2-naphthol or phenol to 1,2,4-triazine, followed by oxidative cyclization. The scope and limitations of this novel coupling reaction have been investigated. F  ...[more]

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