An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines. [Display omitted] •Single-step one-pot gateway synthesis of glochidine and its congeners.•Tandem formation of three C–N bonds and annulation of two rings in a single-step.•Employs the readily available γ-ketoesters and histamine as starting materials.•For the first time, the unknown biological activity was explored for this rare class of compounds.