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Molecular complexity is commonly invoked as a milestone in drug discovery and R D programs. Behind this general concept, precise parameters can be specifically scrutinized. In fact, the design of an active substance can be rationalized by its shape complementary with the targeted receptor. Hence, tridimensional compounds with a reduced aromatic character are more prone to clinical success. If saturation strategies are considered as the traditional approach, a recent concept recently blossomed; namely the dearomative enlargement of aromatic rings. Our group was recently involved in the development of innovative sequences enabling the incorporation of nitrogen atoms for the synthesis of 1,2-diazepines from readily available pyridines enabled by photochemical irradiation. More recently, we could improve this protocol by replacing chlorinated activating groups by isocyanates. As a result, the overall yields were significantly enhanced and the stability of the formed heterocycles greatly improved. Moreover, the protocol became amenable to prepare grams of product. Having established a robust route to synthesized this underconsidered motif, we just launched a research program aiming at merging the best of the 2 approaches: the saturation and the atom insertion. Indeed, the 1,2-diazepine ring can be regarded as an imine, an olefin, or even a diene; thus, opening a plethora of new opportunities to generate Csp3 stereocenters. Altogether, this missing link should remarkably increase both the complexity and the selectivity of the newly formed molecules and place the 1,2-diazepines on the foreground as valuable targets for future clinical successes. A first effort has been recently accomplished by our group for the synthesis of 1,2-diazepine-fused b-lactams via a Staudinger-type [2+2] reaction.