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Photoassisted synthesis of complex polyheterocyclic molecular architectures via excited state intramolecular proton transfer (ESIPT) is for the first time implemented for the reactions of  o -keto phenols. This adds the 2,5-epoxybenzoxacine core to the previously obtained 2,5-epoxybenzazocine cores and offers rapid access to primary photoproducts which lend themselves to diverse yet simple postphotochemical modifications to further grow the complexity of the target structures, specifically – access to polyheterocycle-carbohydrate chimeras containing up to five contiguous stereogenic centers and benzazocine or benzoxacine heterocyclic cores.

pure and applied chemistry

Polyheterocycle-carbohydrate chimeras: photoassisted synthesis of 2,5-epoxybenzoxacines and 2,5-epoxybenzazocine scaffolds and their postphotochemical hydroxylations