Synthesis Of Pyrrolo-and Pyrrolidino[1,2-a] Quinolin-1-one Via Intermolecular [4+2] Reactions Of N-Acyliminium Cations With Olefins

The forcus of this thesis is on the [4+2] reactions of N-acyliminium cations with olefins and the synthesis of pyrrolo-and pyrrolidino[1,2-a]quinolin-1-ones .(1) The [4+2] reactions of N-acyliminium cations, produced from 5-hydroxy -1-arylpyrrol-2-ones or 5-hydroxy-1-arylpyrrolidin-2-ones in the presence of BF₃·OEt₂ with olefins has been studied. A new method for the synthesis of pyrrolo[1,2-a]quinolinl-ones or pyrrolidino[1,2-a]quinolin1-ones has been developed in moderate to good yields at ambient temperature.(2) The enantioseletive synthesis of the pyrrolidino [1,2-a]quinolin1-ones and starting from L-malic acid and L-tartaric acid has been tried.(3) The condensation reactions of active methylene compounds such as 1,3-dicarbonyls withω-hydroxylactam 2,3-dihydro-3-hydroxy -2-arylisoindol-1-one under the influence of lewis acid BF₃·OEt₂ have been tried.