Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines withortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.
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.
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Matthew T
MT
Richers
Indubhusan
I
Deb
Alena Yu
AY
Platonova
Chen
C
Zhang
Daniel
D
Seidel
Aminals; C–H bond functionalization; Friedländer condensation; Quinazolinone alkaloids; Redox Isomerization