Synthesis of Benzotriazepine Derivatives via [4+3] Cycloaddition of Aza-o-quinone Methide Intermediates and Azomethine Imines

Abstract

An efficient and unprecedented [4+3] cycloaddition between in situ generated aza-o-quinone methides and azomethine imines via an aza-Michael/aminalization sequence has been developed. The scalable protocol allows to expeditiously assemble a valuable heterocyclic system incorporating tetrahydroisoquinoline and benzotriazepine scaffolds in good to excellent yields under mild conditions.

Key words

[4+3] cycloaddition - aza-o-quinone methide - azomethine imine - triazepine - 7-membered heterocycles

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