Since the exhaustive computational enumeration of heteroaromatic ring systems first described by Pitt et al. several articles have detailed the enumeration of ring systems, yet few follow up articles have proposed syntheses to access the motifs described. We examined 'Ring Breaker' in the context of novel ring systems, the so-called 'Rings of the Future'. Having trained the model on patent data up to 2016, we selected two novel ring systems from the literature for which the synthesis were reported in 2016, and ensured that they were not present in the training dataset. Rather than predicting the full synthetic route, we focused on the ring-forming step. We found the first applicable template in both cases corresponded to the disconnection reported in the literature (Figure ). This further demonstrates the applicability of 'Ring Breaker' to previously unseen ring systems and shows how the approach can be used as an idea generator to explore novel ring-based scaffolds. Furthermore, the literature or patent precedent allows for researchers to lookup reaction conditions and experimental procedures.