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Operationally friendly protocols to produce libraries of novel small molecules with high molecular complexity are in huge demand for the interrogation of biological systems. As such, development of new MCRs and post-condensation modification of the MCR products have proven fruitful in the quest for new molecular probes and their expedited progression along the drug discovery value chain. The products thereof have found their way into numerous corporate compound collections. Crixivan (Indinavir), an antiretroviral, and Xylocaine (Lidocaine), a local anesthetic, are two examples of drugs derived from an MCR that have been marketed. The research topic of this dissertation encompasses the design and development of fifteen novel drug-like chemotypes in an operationally friendly, green, and expedited (≤ 3 synthetic operations) manner involving the Ugi MCR coupled with MAOS and high-throughput purification platforms. Over 500 drug-like small molecules (purity > 90% based on UV 214 nm and ELSD) have been synthesized, purified, and submitted to the NIH MLSMR for further biological evaluation against protein targets of interest. Furthermore, non-electrochemical carbamate oxidations enabling formation of N-acyliminium ion precursors, which are reactive intermediates that form the basis of a multitude of synthetic routes to natural products, have also been developed.