Rh(II)-catalyzed condensation of 3-diazotetramic acids with nitriles delivers novel druglike 5,6-dihydro-4H-pyrrolo[3,4-d]oxazol-4-ones

Previously reported 3-diazotetramic acids have been successfully involved in Rh(II)-catalyzed condensa-tion with aliphatic and aromatic nitriles delivering compounds bearing a hitherto unexplored polysubsti-tuted fused oxazole scaffold. The latter was found to be somewhat labile to the addition of nucleophiles (water and benzylamine) which leads to oxazole ring opening and may constitute an entry into polysub-stituted pyrrolinones after due investigation of scope. (c) 2023 Published by Elsevier Ltd.

Automated summary

Previously reported 3-diazotetramic acids have been successfully used in Rh(II)-catalyzed condensation reactions with aliphatic and aromatic nitriles, leading to the synthesis of polysubstituted fused oxazole compounds. The resulting oxazole scaffold was found to be susceptible to nucleophilic addition (such as water and benzylamine), resulting in ring opening and the potential formation of polysubstituted pyrrolinones after further investigation of its scope.