Transannulation approach toward fused pyrroloheterocycles

ORGN 434

Stepan N. Chuprakov, schupr1@uic.edu and Vladimir Gevorgyan, vlad@uic.edu. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061
It has been demonstrated that 1,2,3-triazolo[1,5-a]pyridines 1 may serve as stable, readily available and effective precursors for Rh-carbenoids containing pyridyl substituent. In reaction with terminal alkynes, depending upon conditions, triazole 1 either gives [2+1] cycloaddition product, cyclopropene 2, or undergoes unprecedented transannulation reaction to form indolizine 3 directly. Additionally, it has been found that 2 in a presence of Cu(I) salts can be efficiently transformed into 3. The scope, limitations and possible mechanisms of these novel transformations will be discussed.