title: Synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles from (hetero)arylacrylic acids.
abstract: A three-step method for the synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles is described. Easily accessible bis(trimethylsilyl)acetylene and acrylic acid derivatives are used as starting materials for the preparation of mono- and disubstituted 5-(trimethylsilyl)pent-1-en-4-yn-3-ones. Oxidative phthalimidoaziridination of these enynones provides the key 2-acyl-1-phthalimidoaziridines that are further utilized in the thermal expansion of the three-membered ring to furnish the target functionalizable oxazoles.
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia.
authors.forename: Alena S
authors.initials: AS
authors.lastname: Pankova
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia.
authors.forename: Alexander Yu
authors.initials: AY
authors.lastname: Stukalov
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia.
authors.forename: Mikhail A
authors.initials: MA
authors.lastname: Kuznetsov
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000179:Acrylates; D010080:Oxazoles; C036658:acrylic acid