New Octahydropyrido[3,4-b]acridine Scaffolds for Combinatorial Chemistry

Abstract

Friedländer reaction of aminobromobenzaldehydes with an optically active decahydroisoquinolone building block gave new octahydropyrido[3,4-b]acridines with quantitative regioselectivity. The products define a platform for combinatorial chemistry. Bromine functions could be reacted further using Suzuki, Heck, Sonogashira, and Buchwald-Hartwig reactions as well as cyanations. The secondary amino function was deprotected and coupled with amino acids and benzoic acid derivatives. A small model library has been prepared.

Investigation into a Tetrahydroquinazoline Scaffold

“…Application of elevated temperature lead to unspecific reduction of the aromatic rings. Thus, we tried the reduction with base metals like zinc [6a] or iron, [12] but only sluggish conversion was observed. When using trichlorosilane in the presence of triethylamine as reducing agent, [13] compound 11 c was formed, although it could be isolated only in moderate yield (45 %, [a] Yield of isolated product.…”