title: Reactions of o-quinone methides with pyridinium methylides: a diastereoselective synthesis of 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans.
abstract: A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.
authors.affiliation: Department of Organic Chemistry, Samara State Technical University, 244 Molodogvardeiskaya Street, 443100 Samara, Russian Federation. vosyanin@mail.ru
authors.forename: Vitaly A
authors.initials: VA
authors.lastname: Osyanin
authors.forename: Dmitry V
authors.initials: DV
authors.lastname: Osipov
authors.forename: Yuri N
authors.initials: YN
authors.lastname: Klimochkin
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011726:Pyridinium Compounds / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C584628:1,2-dihydronaphtho(2,1-b)furan; D001572:Benzofurans; D005663:Furans; D009281:Naphthalenes; D011726:Pyridinium Compounds; D011809:Quinones; C043168:coumaran