Optional Synthesis of 2- or 5-Substituted 3-Bromopyrroles via Bromine-Lithium Exchange of N-Benzenesulfonyl-2,4-dibromopyrrole
スポンサーリンク
概要
- 論文の詳細を見る
The regioselective bromine–lithium exchange of N-benzenesulfonyl-2,4-dibromopyrrole (6) with n-BuLi followed by treatment with various electrophiles gave 5-substituted 3-bromopyrroles (5) in excellent yields. In contrast, the sequential treatment of 6 with n-BuLi and diisopropylamine followed by quenching with electrophiles produced regioisomeric 2-substituted 3-bromopyrroles (3) selectively. The latter reaction can be rationalized by the rapid equilibration of the C-5 lithio species (4) to the more stable C-2 lithio species (2) in the presence of diisopropylamine.
- 日本複素環化学研究所の論文
- 2012-08-21
日本複素環化学研究所 | 論文
- Reactions of 2-Triphenylphosphoimino-1-azaazulenes with Aryl Isocyanates and Aryl Isothiocyanates
- Synthesis and some reactions of 11-azacyclohept[a]azulen-3(3H)-ones and evaluation of their cytotoxic activity against HeLa S3 cells
- Palladium-catalyzed heteroarylamination of ethyl 2-chloro-1-azaazulene-3-carboxylate and annulation of heteroarylamino-1-azaazulenes
- Synthesis of [poly(2-pyridyl)-substituted]-1-azaazulenes
- Heteroarylamination and heteroarylsulfidation of 2-chloro-1-azaazulenes