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Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction. 2021
Matteo Faltracco, and
Said Ortega-Rosales, and
Elwin Janssen, and
Răzvan C Cioc, and
Christophe M L Vande Velde, and
Eelco Ruijter
Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute of Molecular & Life Sciences (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands.
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.
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