Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-Wittig reactions.
Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.
Gil
Carmen
C
Kekulé-Institut für Organische Chemie und Biochemie, Rheinischen Friedrich-Wilhelms-Universität, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany.
Bräse
Stefan
S
D014151:Anti-Anxiety Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D009943:Organophosphorus Compounds / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis; D014226:Triazenes / Q000737:chemistry
D014151:Anti-Anxiety Agents; D001386:Azides; D001570:Benzodiazepinones; D009943:Organophosphorus Compounds; D011799:Quinazolines; D014226:Triazenes; C061896:triphenylphosphine; C025696:2,3-trimethylene-4-quinazolone