Heterocyclic compounds are prevalent in all biological systems and are essential to the maintenance of life. The synthesis of natural products is continuously pursued to make available large enough quantities to be used in medicinal research. The functionalization of available starting materials provides an approach to a synthetic plan in which methylheteroaromatics offer a simple keystone. At present the use of sodium hydride for the introduction of appropriate building blocks onto a side-chain in heteroaromatics does not appear to have been studied. In this connection the acylation of a series of methylheteroaromatics was studied using sodium hydride in dimethoxyethane (DME). The use of multiple anions of methylheteroaromatics was also investigated in several model systems. These methods offer a convenient means of drug design in a variety of different heterocycles of medicinal importance.