Synthesis of novel 1H-pyrrolizine-5-carboxamides and their antimicrobial properties.

A variety of N-aryl-7-cyano-2,3-dihydro-1H-pyrrolizine-5-carboxamides 6, 8-11 were synthesized through the reaction of the 2-amino derivatives 3 with acid chlorides, aromatic and aliphatic aldehydes. In addition, 3 could directly obtained through the reaction of 2-pyrrolidinylidenepropanedinitrile (1) with chloroacetanilides 2a,b. However, reaction of 1 with-chloropropionanilide 2c gave the open-chain compound 5. The antimicrobial properties of the newly prepared compounds were screened against a variety of Gram positive, Gram-negative bacteria and yeast. Some of the prepared compounds (8a, 8c and 9a) show moderate activity against the tested Gram-positive bacteria (Staphylococcus aureus and/or Coagulase negative Staphylococcus). In addition, other compounds (6a, 9d and 9e) exhibit slight (weak) activity against Coagulase negative Staphylococcus.