Carbazoles have recently become an interesting scaffold to work with in the field of medicinal chemistry, especially as antibiotic adjuvants. Current syntheses of novel carbazole derivatives involve coupling reactions, one of which utilizes a palladium-catalyzed nitroarene. While effective for a short time, the current methods are no longer viable for future experiments because of being cost and time intensive. There are a limited number of commercially available carbazole derivatives, which brings interest to synthesizing carbazole analogs to increase the library of derivatives. This can be done through a two-step synthesis process involving the photo-redox Chan-Evans-Lam coupling reaction and a palladium-catalyzed synthesis, which cyclizes the intermediate into the product. The coupling reaction combines derivatives of aniline and phenylboronic acid, with the addition of catalysts, to create a substituted diphenylamine. The diphenylamine derivative then undergoes a palladium-catalyzed synthesis to form the final bond, significant of a carbazole. Reaction conditions have been optimized to observe what can be added to decorate the exterior of the carbazole parent. Thus far, several diphenylamines have been created through the initial coupling reaction and patterns are emerging with selectivity for positions and groups. These diphenylamine derivatives are currently undergoing the second step of the synthesis procedure. Once cyclized, these compounds will be tested for their potential adjuvant activity. Synthetic details, optimized methodology, and biological data (if available) will be presented for completed compounds. Future directions will be to create a library of carbazole derivatives and to explore alternate methodologies for the creation of the carbazole.

Methodology optimization for the synthesis of novel carbazole derivatives utilizing the Chan-Evans-Lam coupling reaction to target antibiotic resistance

ACS Spring 2022

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