A facile synthesis of 9-dialkylamino-9H-pyrrolo[1,2-a]indoles via iminium salts generated from 2-(pyrrol-1-yl)benzaldehydes and secondary amine hydrochlorides in the presence of NaI/TMSCl/Et3N

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

“…51 A modification of the method discussed above relies on using dialkylamines and in situ generated iodotrimethylsilane. 53,54 The first step of the reaction was amine silylation, leading to quantitative yield of the dialkylaminotrimethylsilane which then reacted with the…”

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

“…Reaction of 2‐(pyrrol‐1‐yl)benzaldehydes 214 with hydrochlorides of secondary amines in the presence of chlorotrimethylsilane, sodium iodide, and triethylamine produces 9‐amino‐9 Н ‐pyrrolo[1,2‐ a ]indoles 216 via iminium salts 215 . The authors discovered that hydrochlorides of secondary amines produce quaternary salts 215 .…”

TMSCl-Catalyzed synthesis of substituted quinolines from arylimines and enolizable aldehydes

“…Chlorotrimethylsilane (TMSCl) has been used as a mild and efficient promoter for various organic reactions. [39][40][41][42][43] It has also been reported as a mild useful and inexpensive Lewis acid catalyst for the synthesis of biologically important compounds. [44][45][46] In continuation of our interest in TMSCl-promoted syntheses of nitrogen-containing heterocyclic compounds, 47 herein we report a simple, highly efficient and environmentally friendly process for the preparation of biologically important quinolines from arylimines and enolizable aldehydes using TMSCl as a Lewis acid catalyst (Scheme 1).…”