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Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction.

ABSTRACT: An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives.

SUBMITTER: Faltracco M

PROVIDER: S-EPMC8056386 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction.

Faltracco Matteo M Ortega-Rosales Said S Janssen Elwin E Cioc Răzvan C RC Vande Velde Christophe M L CML Ruijter Eelco E

Organic letters 20210331 8

An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives. ...[more]

PMID: 33787266

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