|
Title
|
Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition
|
|
Type
|
JournalPaper
|
|
Keywords
|
2-(aryloxy)fumarates - 2-(alkyl- or arylthio)fumarates - azomethine ylides - spiro compounds - pyrrolizidines - pyrrolidines - DFT calculations
|
|
Abstract
|
Dimethyl 2-(aryloxy)fumarates and dimethyl 2-(alkyl- or arylthio)fumarates are shown to be efficient dipolarophiles in 1,3-dipolar cycloaddition reaction with azomethine ylides, which are generated by the reaction of isatin with the secondary amino acids proline or sarcosine. In these reactions, dimethyl 2-(alkyl- or arylthio)fumarates afforded spirooxindolopyrrolizidines or -pyrrolidines in high yields with excellent regioselectivities, while dimethyl 2-(aryloxy)fumarates produced mixtures of regioisomers. DFT calculations at the B3LYP/6-31G(d,p) level were consistent with the observed results. Tri- and tetracyclic compounds were obtained through regio- and stereoselective intramolecular cycloaddition of O-vinylic salicylaldehyde with secondary amino acids
|
|
Researchers
|
Mahgol Tajbakhsh (Fifth Researcher), Kamal Alimohammadi (Fourth Researcher), Mahshid Hamzehloueian (Third Researcher), Marzieh Sadatshahabi (Second Researcher), Yaghoub Sarrafi (First Researcher)
|