title: Gold-Catalyzed Benzylic Azidation of Phthalans and Isochromans and Subsequent FeCl3-Catalyzed Nucleophilic Substitutions.
abstract: The benzylic positions of the phthalan and isochroman derivatives (1) as benzene-fused cyclic ethers effectively underwent gold-catalyzed direct azidation using trimethylsilylazide (TMSN3) to give the corresponding 1-azidated products (2) possessing the N,O-acetal partial structure. The azido group of the N,O-acetal behaved as a leaving group in the presence of catalytic iron(III) chloride, and 1-aryl or allyl phthalan and isochroman derivatives were obtained by nucleophilic arylation or allylation, respectively. Meanwhile, a double nucleophilic substitution toward the 1-azidated products (2) occurred at the 1-position using indole derivatives as a nucleophile accompanied by elimination of the azido group and subsequent ring opening of the cyclic ether nucleus produced the bisindolylarylmethane derivatives.
authors.affiliation: Gifu Pharmaceutical University.
authors.forename: Shota
authors.initials: S
authors.lastname: Asai
authors.forename: Yuki
authors.initials: Y
authors.lastname: Yabe
authors.forename: Ryota
authors.initials: R
authors.lastname: Goto
authors.forename: Saori
authors.initials: S
authors.lastname: Nagata
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Kita
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Sawama
mesh_terms: D001386:Azides / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D002839:Chromans / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D010797:Phthalimides / Q000737:chemistry*
chemical_list: D001386:Azides; D001593:Benzyl Compounds; D002712:Chlorides; D002839:Chromans; D005290:Ferric Compounds; D010797:Phthalimides; D006046:Gold; C024555:ferric chloride; C005020:folpet