Transformations like pyrazole-to-furan are illustrative. The development of new methodologies to effect transformations of this type would enable access to areas of chemical space that are currently underexplored. Intuitive single-atom alterations, such as the conversions of pyridine-to-pyrrole or pyrimidine-to-pyrrole, tend to produce a slightly higher percentage of known compounds and would therefore be judged as of lesser value. Nonetheless, these transformations are extremely valuable in discovery campaigns due to the precision afforded by single-atom edits in the context of late-stage diversification. Importantly, the transformations identified herein would enable interconversions between many heteroaromatics that are prevalent in FDA approved drugs, especially in the context of the aforementioned ring expansion methodologies. Synthetic methods for transformations that are complementary to those identified as potentially impactful in this report are continuing to emerge. Considered together, the now quantified potential impact of these transformations highlights the necessity of continued development of new skeletal editing reactions. The analysis presented here may serve as a useful starting point for the community to use quantitative metrics to quantify the impact of different core-atom transformations of heteroaromatics in compound diversification campaigns.