title: Regioselective Transition-Metal-Free Synthesis of 2-(Trimethylsilylmethylene)pyrrol-3-ones by Thermal Cyclization of Acetylenic Enamines.
abstract: Acetylenic enamines generated in situ from readily available enynones and primary amines undergo thermal cyclization in diphenyl ether providing easy access to 4-aryl-2-(trimethylsilylmethylene)-1,2-dihydro-3H-pyrrol-3-ones. This reaction is inherently versatile, allowing for variations of substituents in both enynone and amine. Full regioselectivity along with short reaction time (1-2 h) and simple workup afford single products in good to excellent isolated yields. Fluorescent properties of the obtained compounds were studied.
authors.affiliation: Institute of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia.
authors.forename: Pavel R
authors.initials: PR
authors.lastname: Golubev
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: Mikhail A
authors.initials: MA
authors.lastname: Kuznetsov
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000603389:2-(trimethylsilylmethylene)pyrrol-3-one; D000588:Amines; D011758:Pyrroles; D014297:Trimethylsilyl Compounds; D000114:Acetylene