title: Metal-free entry to phosphonylated isoindoles by a cascade of 5-exo-dig cyclization, a [1,3]-alkyl shift, and aromatization under microwave heating.
abstract: [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.
authors.affiliation: Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
authors.forename: Nicolai
authors.initials: N
authors.lastname: Dieltiens
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
mesh_terms: 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*
chemical_list: D006841:Hydrocarbons, Aromatic; D007211:Indoles; D063065:Organophosphonates; C044736:phenylacetylene; D000114:Acetylene