Article citationsMore >>

Perchellet, E.M.; Magill, M.J.; Huang, X.; Brantis, C.E.; Hua, D.H.; Perchellet, J.P. “Triptycenes; a novel synthetic class of bifunctional anticancer drugs that inhibit nucleoside transport, induce DNA cleavage and decrease the viability of leukemic cells in the nanomolar range in vitro” Anti-Cancer Drugs, 10, 749-766, 1999.

has been cited by the following article:

Article

Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers

1Department of Chemistry and Biochemistry, Seton Hall University, South Orange, New Jersey, USA


World Journal of Organic Chemistry. 2021, Vol. 9 No. 1, 1-5
DOI: 10.12691/wjoc-9-1-1
Copyright © 2021 Science and Education Publishing

Cite this paper:
Alfredo Mellace, James E. Hanson. Trisubstituted Triptycenes: Toward the Preparation of Three-Dimensional Dendrimers. World Journal of Organic Chemistry. 2021; 9(1):1-5. doi: 10.12691/wjoc-9-1-1.

Correspondence to: James  E. Hanson, Department of Chemistry and Biochemistry, Seton Hall University, South Orange, New Jersey, USA. Email: james.hanson@shu.edu

Abstract

A synthesis of benzyl trisubstituted triptycenes is described. These triptycenes are precursors for producing a first generation (G1) poly(triptycylether) dendrimer, a derivative of known poly(arylether) dendrimers. The molecule necessary for the further elaboration into the eventual dendrimer is a carboxylic acid ester triptycene terminated with two ether substituents on another ring; the zero generation (G0). The synthesis begins with formation of the Diels-Alder adduct of benzoquinone and methyl 2-anthroate. This adduct is aromatized under basic conditions and the resulting anion trapped with a benzyl halide as an electrophile to form the trisubstituted triptycene. Access to the trisubstituted system is obtained through a highly improved, efficient and chromatography free preparation of anthracene derivatives, mainly methyl 2-anthroate.

Keywords