Heterocycles are important structural scaffolds present in biologically active substances, natural products and pharmaceuticals. In particular, 1,3,4-oxadiazines derivatives are present in MAO inhibitors or anticancer drugs, among others. Despite of this biological activity, the catalytic methods to access 1,3,4-oxadiazinanes remain elusive to our knowledge. A formal [3+3] cyclization reaction of diaziridine and quinones has been developed offering 1,3,4-oxadiazinanes in generally high yields In this transformation, scandium(III) activates diaziridine yielding an intermediate ylide, which undergoes 1,3-dipolar cycloaddition with benzoquinone. Among the Lewis acids that can perform the cleavage of diaziridine, scandium catalysts stand out as eco-friendly catalyst with low toxicity, recyclability and cost-effective transition metal. The synthetic method developed in this work provides a new synthetic route to access heterocycles containing three heteroatoms.

Scandium-catalyzed (3+3)-annulation of diaziridines with benzoquinones

ACS Spring Meeting 2021

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