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

Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel

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

Synthesis (Stuttg). 2013 Oct 6;45(13):1430-1748.

Authors

Matthew T Richers¹, Indubhusan Deb, Alena Yu Platonova, Chen Zhang, Daniel Seidel

Affiliation

¹ Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.

PMID: 24052668
PMCID: PMC3774014

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.

Keywords: Aminals; C–H bond functionalization; Friedländer condensation; Quinazolinone alkaloids; Redox Isomerization.

Grants and funding

R01 GM101389/GM/NIGMS NIH HHS/United States