Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes.
Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I2, ICl, NIS, Br2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with I2 and simple olefins or alkynes.
Yue
Dawei
D
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Della Ca
Nicola
N
Larock
Richard C
RC
D000114:Acetylene / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis*; D003500:Cyclization; D009281:Naphthalenes / Q000138:chemical synthesis*
D000447:Aldehydes; D001578:Benzopyrans; D009281:Naphthalenes; D000114:Acetylene