23949-31-7Relevant articles and documents
Gold-catalyzed benzylic azidation of phthalans and isochromans and subsequent FeCl3-catalyzed nucleophilic substitutions
Asai, Shota,Yabe, Yuki,Goto, Ryota,Nagata, Saori,Monguchi, Yasunari,Kita, Yasuyuki,Sajiki, Hironao,Sawama, Yoshinari
, p. 757 - 761 (2015)
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.