Our research focuses on the development of new methodology in synthesizing nitrogen-containing heterocycles known as alpha-carbolines. We have previously reported a transition-metal catalyzed cyclization strategy to synthesize a different isomer, beta-carbolines. This strategy can be utilized for alpha-carboline synthesis through the formation of a cyanamide precursor molecule in five steps. From this precursor, we describe two parallel strategies for the addition of an iodobenzene substituent and subsequent [2+2+2] cyclization: a stepwise sequence using a Sonogashira cross-coupling followed by cyclization with a Rh(I) catalyst, and tandem catalysis using Pd(0). We first optimized the five-step synthesis of the cyanamide precursor to efficiently obtain the desired compound, followed by the optimization of the conditions for tandem catalysis by changing the solvent, catalyst, stoichiometry, temperature, and time. Next, we screened different solvents for Rh(I)-catalyzed cyclization. Finally, we report the synthesis of a series of different substituted alpha-carbolines via both pathways and compare the efficiency of the two strategies for each substituent. <br/>

Convenient synthesis of 2-aryl-alpha-carbolines via synergistic methods

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.