Polyfunctional imidazoles: XI. Reaction of 1-aryl-4-chloro-5-(2-nitrovinyl)-1H-imidazoles with nonstabilized azomethine ylides. Synthesis of (1-aryl-4-chloro-1H-imidazol-5-yl)-substituted nitropyrrolidines and nitropyrrolizines

摘要

1-Aryl-4-chloro-5-(2-nitrovinyl)-1H-imidazoles reacted with azomethine ylide generated from sarcosine and formaldehyde to afford 1-aryl-4-chloro-5-(4-nitropyrrolidin-3-yl)-1H-imidazoles. The reaction of 1-aryl-4-chloro-5-(2-nitrovinyl)-1H-imidazoles with azomethine ylide generated from L-proline and isatin gave 2'-(1-aryl-4-chloro-1H-imidazol-5-yl)-1'-nitro-1',2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizin]-2(1H)-ones with high regioselectivity. The latter reaction was analyzed by calculating orbital coefficients and global and molecular reactivity indices of the dipole and dipolarophile, as well as the energies of the initial reactants, transition states, and products.