Synthesis 2013; 45(13): 1730-1748
DOI: 10.1055/s-0033-1338852
feature article
© Georg Thieme Verlag Stuttgart · New York

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

Matthew T. Richers
a   Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA   Fax: +1(732)4455312   Email: seidel@rutchem.rutgers.edu
,
Indubhusan Deb
a   Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA   Fax: +1(732)4455312   Email: seidel@rutchem.rutgers.edu
,
Alena Yu. Platonova
a   Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA   Fax: +1(732)4455312   Email: seidel@rutchem.rutgers.edu
b   Department of Organic Synthesis Technology, Ural Federal University, Yekaterinburg, 620002, Russian Federation
,
Chen Zhang
a   Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA   Fax: +1(732)4455312   Email: seidel@rutchem.rutgers.edu
,
Daniel Seidel*
a   Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA   Fax: +1(732)4455312   Email: seidel@rutchem.rutgers.edu
› Author Affiliations
Further Information

Publication History

Received: 14 March 2013

Accepted after revision: 01 May 2013

Publication Date:
10 June 2013 (online)


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

Supporting Information

 
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