Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with o-Aminobenzaldehydes: Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone, and Ruteacarpine

Dedicated to Prof. Scott E. Denmark on the occasion of his 60^th birthday

Abstract

Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal­ products are precursors for various quinazolinone alkaloids and their analogues.

Key words

C–H bond functionalization - redox isomerization - aminals­ - quinazolinone alkaloids - Friedländer condensation

• References


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