According to the proposed reaction mechanism (see Figure .a.), imine (IM1) is first formed by a nucleophilic addition of an amine to the carbonyl group of a ketone under reaction conditions. The newly formed imine can then undergo an imine-enamine tautomerization to form an enamine intermediate (IM2). Sulfonyl azide reacts with the enamine via a dipolar cycloaddition to form a triazoline intermediate (IM3). Finally, the product is formed in a ring opening reaction together with the release of diazomethane gas. We first set out to verify the likelihood of the ring closing and opening steps by identifying the release of diazomethane. Based on literature precedents, we aimed to intercept diazomethane in situ by reacting it with benzoic acid, which was added to the reaction mixture to afford the corresponding ester (See Figure .b. and Scheme S4 in SI for further details). Methyl benzoate was indeed detected under these modified reaction conditions and amidine formation was not affected by the presence of benzoic acid leading to similar yields, which indicated that the cyclization/de-cyclization steps in the mechanism were plausible.