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J Am Chem Soc. 2013 Aug 28;135(34):12548-51. doi: 10.1021/ja406131a. Epub 2013 Aug 19.

Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

Abstract

We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.

PMID:
23957711
PMCID:
PMC3789141
DOI:
10.1021/ja406131a
[Indexed for MEDLINE]
Free PMC Article

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