The Ru-catalyzed ring-closing metathesis reaction (RCM) and a Pd-catalyzed annulation called the Heck reaction are known as powerful synthetic tools. Our research group discovered a new way how these two reactions performed in a sequence could be used for an efficient preparation of N-heterocycles. The heterocycles are of interest as potential medicinal agents. The work reported herein aimed to improve the efficiency of this sequence by performing both the RCM and the Heck reaction as a one-pot operation, eliminating separation and purification steps that previously had to be performed following the RCM reaction. After much experimentation we established optimum reaction conditions that allow the Heck reaction to be performed in the same solvent as the prior RCM step. Utilizing these conditions, a sequential one-pot (!) RCM/Heck reaction was demonstrated providing high yields of the desired heterocyclic products in excellent purity. Extension of this one-pot RCM/Heck synthetic strategy to the construction of different types of N-heterocyclic structures featuring a bridged core has been also investigated. 

Development of a one-pot sequential transition metal catalyzed reaction for synthesis of biologically active Hhterocycles

245th National Meeting (2013)

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