Acyl azides: application to the synthesis of various heterocycles

Dengiz, Çağatay
Pyrazoles, isoindolinones, benzodizepinones and dihydroquinolinones are very important heterocycles for their biological properties. Many pharmaceutical agents include these units as core structures. Reactive molecules such as acyl azides, free radicals and formyl groups are used as key step reactants in these studies. Regiospesific hydrolysis and esterifications are used to reach target starting materials. Two different methodology are used for critical ring closure steps. Benzodiazepinones, and isoindolinones are obtained by base mediated ring closure reactions whereas thionyl chloride mediated procedure is used for dihydroquinolinones. Moreover, chloroacetonylation of the double bonds is also examined. Addition of acetylacetone to various alkenes was performed with in the presence of Mn(OAc)3 and HCl. Removal of one of the acetyl groups with ammonia under very mild conditions provided compounds derived from chloroacetonylation of the double bonds.