Metal-free entry to phosphonylated isoindoles by a cascade of 5-exo-dig cyclization, a [1,3]-alkyl shift, and aromatization under microwave heating.
[reaction: see text] When o-ethynylbenzyl alpha-aminophosphonates are heated under microwave conditions, a rearrangement occurs which results in the formation of phosphonylated isoindoles. The rearrangement consists of a 5-exo-dig cyclization followed by a [1,3]-alkyl shift and finally aromatization.
Dieltiens
Nicolai
N
Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
Stevens
Christian V
CV
D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D006361:Heating; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D008872:Microwaves; D008956:Models, Chemical; D063065:Organophosphonates / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D007211:Indoles; D063065:Organophosphonates; C044736:phenylacetylene; D000114:Acetylene