Diazoxide—the pharmacological reference compound for the benzothiadiazine class of ATP-sensitive K⁺ channel openers—is a well known antihypertensive agent which inhibits the release of insulin from the pancreas while inducing hypoglycemia.  Reasoning that the 3D structure of this heterocyclic drug could well serve as a template for the development of even more useful new antihypertensives, we are preparing boron-for-sulfur replacement analogs of Diazoxide as structural mimics.  Efforts to synthesize these 2,4,1-oxaza- and diazaborine heterocycle Diazoxide mimics from 3-chlorobenzeneboronic acid supported by multinuclear FT-NMR will be presented.