Synthesis of 6‐Aminoindolo[2,1‐a]isoquinoline‐5‐carbonitriles by the Cu‐Catalyzed Reaction of 2‐(2‐Bromophenyl)‐1H‐indoles with CH₂(CN)₂

Abstract

A series of 6‐aminoindolo[2,1‐a]isoquinoline‐5‐carbonitriles 4 have been prepared by treatment of 2‐(2‐bromophenyl)‐1H‐indoles 1, available from 1‐(2‐bromophenyl)ethanones or 1‐(2‐bromophenyl)propan‐1‐ones by using Fischer indole synthesis, with propanedinitrile in the presence of a catalytic amount of CuBr and an excess of K2CO3 in DMSO at 100°.

Palladium-Catalyzed Monoarylation of Arylhydrazines with Aryl Tosylates

“…2-(2-Bromo-4,5-dimethoxyphenyl)-1H-indole. 28 An oven-dried 250 mL single-neck round-bottom flask equipped with a Tefloncoated magnetic stir bar was charged with 1-(2-bromo-4,5dimethoxyphenyl)ethan-1-one (7.77 g, 30.0 mmol) and phenylhydrazine (3.6 mL, 36.0 mmol) via syringe. Phosphoric acid (15.0 mL) was added slowly, and the reaction mixture was stirred for 30 min.…”