New Building Blocks Based on Truxene Cores: Synthesis of Functionalized syn-Tri- and Hexasubstituted Derivatives

Hexasubstituted truxenes are obtained in one step by alkylation of the potassium anion of truxene. Subsequent derivatization provides truxene derivatives with six carboxy, amino, or hydroxy groups at their peripheries. Alkylation of syn-5,10,15-tribenzyl derivatives with a different benzyl bromide derivative affords mixtures of anti- and syn-hexasubstituted truxenes. Truxenes with phenols or benzoquinone groups have also been synthesized by starting from truxenetrione.