Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates

Abstract

A series of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines were synthesized in high-to-excellent yields (up to 99%) starting from the corresponding ferrocenoylethyl aryl amines. These Mannich bases were reduced (NaBH4) to the corresponding 3-(arylamino)-1-ferrocenylpropan-1-ols and submitted to an intramolecular cyclization prompted by acetic acid, proceeding via the corresponding alpha-ferrocenyl carbenium ion intermediates. Subsequently, the obtained tetrahydroquinolines were smoothly oxidized (aromatized) by means of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to provide the corresponding 4-ferrocenylquinolines (up to 93%). (C) 2017 Elsevier Ltd. All rights reserved.