Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values

The AgOTf-catalyzed reaction of C-2 substituted pyrrole hydrazones having an N-propargyl group was studied. The selective 6-endo-dig mode of cyclization was observed, giving rise to the formation of pyrrole-fused C,N-cyclic azomethine imine derivatives. The reaction of one azomethine imine derivative with various dipolarophiles resulted in the formation of cycloadducts having a pyrazolopyrrolopyrazine skeleton. The aromaticity of C,N-cyclic azomethine imines as well as that of pyrazolopyrrolopyrazines was determined by calculating of nucleus-independent chemical shifts values.