Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes.
J Org Chem, 2013/2/01;78(3):1311-6.
Read ML[1], Gundersen LL
Affiliations
PMID: 23305184DOI: 10.1021/jo3027033
Impact factor: 4.198
Abstract
A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.
MeSH terms
Aza Compounds; Catalysis; Cyclization; Cycloparaffins; Furans; Microwaves; Molecular Structure; Phenanthridines; Stereoisomerism
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