Orthogonal and auto-tandem catalysis: synthesis of dipyrido[1,2-a:2',3'-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation

Kristof T J Loones; Bert U W Maes; Caroline Meyers; Joke Deruytter

doi:10.1021/jo052091u

Orthogonal and auto-tandem catalysis: synthesis of dipyrido[1,2-a:2',3'-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation

J Org Chem. 2006 Jan 6;71(1):260-4. doi: 10.1021/jo052091u.

Authors

Kristof T J Loones¹, Bert U W Maes, Caroline Meyers, Joke Deruytter

Affiliation

¹ Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium.

PMID: 16388645
DOI: 10.1021/jo052091u

Abstract

[reaction: see text] The synthesis of dipyrido[1,2-a:2',3'-d]imidazole and hitherto unknown benzo and aza analogues is described. These relatively complex polycyclic heterocycles could be smoothly prepared in one step from commercially available building blocks. Mechanistically, the developed procedure involves orthogonal (Pd and Cu catalyst) or auto-tandem (Pd catalyst) catalysis via regioselective inter- and intramolecular C-N bond formation.