Derivatives of Fluorene. XI. New Nitrogen Mustards¹

Diazatetraester 1H-Pyrazole Crowns as Fluorescent Chemosensors for AMPH, METH, MDMA (Ecstasy), and Dopamine

“…The starting N,N-bis(2-hydroxyethyl)-9H-fluoren-9-ylamine and N,N-bis(2-hydroxyethyl)(naphth-2ylmethyl)amine were previously prepared by reaction of 9-bromofluorene or 2-(bromomethyl)naphthalene with diethanolamine following a previously reported method. 20 The above aminodiols were then heated to reflux in toluene with butyltin oxide to give a mixture of stannoxanes, which were later reacted with 1H-pyrazole-3,5-dicarbonyl dichloride in dry dimethoxyethane at 60 °C. The corresponding reaction mixtures were then purified as indicated in the experimental part to yield compunds 1 and 2 as crystalline solids (see the Supporting Information).…”

“…The synthesis of 1 and 2 was achieved as depicted in Figure C. The starting N,N -bis(2-hydroxyethyl)-9 H -fluoren-9-ylamine and N,N -bis(2-hydroxyethyl)(naphth-2ylmethyl)amine were previously prepared by reaction of 9-bromofluorene or 2-(bromomethyl)naphthalene with diethanolamine following a previously reported method …”