title: Novel synthesis of 3-substituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ.
abstract: A new method is presented for the regioselective one-pot synthesis of 3-substituted 2,3-dihydrobenzofurans from 2-bromo-1-{2-[(triisopropylsilyl)oxy]phenyl}ethyl nitrate by fluoride-induced desilylation leading to o-quinone methide generation, Michael addition of different C, N, O, and S nucleophiles, and intramolecular 5-exo-tet elimination of a bromide anion. The method has potential synthetic applications in drug discovery.
authors.affiliation: Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina , 451 10 Ioannina, Greece.
authors.forename: Abdul kadar
authors.initials: Ak
authors.lastname: Shaikh
authors.forename: George
authors.initials: G
authors.lastname: Varvounis
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000588730:2-bromo-1-(2-((triisopropylsilyl)oxy)phenyl)ethyl nitrate; D001572:Benzofurans; D045563:Indolequinones; D017646:Organosilicon Compounds; C068040:quinone methide