Synthesis of spiro[4.5]cyclohexadienones with an allene motif via a base-promoted intramolecular ipso-Friedel–Crafts addition of phenols to propargyl bromides

Autor:	Yasumasa Hamada, Zengduo Zhao, Tetsuhiro Nemoto, Takuya Yokosaka, Riliga Wu
Rok vydání:	2013
Předmět:	Allene Organic Chemistry chemistry.chemical_element Alkylation Biochemistry Medicinal chemistry Adduct chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Propargyl Phenols Friedel–Crafts reaction Palladium
Zdroj:	Tetrahedron. 69:3403-3409
ISSN:	0040-4020
Popis:	We developed a novel synthetic method for allenyl spiro[4.5]cyclohexadienone derivatives based on a base-promoted intramolecular ipso-Friedel–Crafts addition of phenols to propargyl bromides. The present spirocyclization proceeded in a CH2Cl2–tert-BuOH mixed solvent system using potassium tert-butoxide as the base, and produced the corresponding spiro[4.5]cyclohexadienone derivatives with an allene motif in up to 99% yield. This-type allenyl spirocycle was also accessible through Pd-catalyzed intramolecular ipso-Friedel–Crafts alkylation when a propargyl carbonate derivative with a naphthol unit was used as a substrate. Acid-promoted skeletal rearrangement of the reaction adducts was also examined.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4af18e0ad9d9e0a7812f9e330d33593d https://doi.org/10.1016/j.tet.2013.02.082 Zobrazit plný text záznamu Full Text from ScienceDirect