N-Phenyl-p-phenylenediamine → 2,3,3a,4,5,9b-Hexahydro-4-(3-hydroxypropyl)-8-phenylamino-furano[3,2-c]quinoline

Participants

Reaction Steps

The mixture of 4-(N-phenylamino)-aniline (2 mmol), 2-hydroxy-tetrahydrofuran (6 mmol) and InCl3 (0.2-0.4 mmol) in water (5 mL) was stirred at room temperature. The reaction was monitored by TLC. After 24 h stirring at room temperature, the reaction mixture was extracted with ethyl ether (3×20 mL). Removal of solvent and flash column chromatography gave 1,2,3,4-tetrahydroquinoline derivatives in 86% yield (cis:trans=46:54).

Provenance & Evidence