RESUMO
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.
Assuntos
Compostos Aza/química , Cicloparafinas/química , Furanos/química , Fenantridinas/síntese química , Catálise , Ciclização , Micro-Ondas , Estrutura Molecular , Fenantridinas/química , EstereoisomerismoRESUMO
The structure of the title compound, C(6)H(6)O(3), has been redetermined at low temperature [room-temperature structure: Maartmann-Moe (1965 â¶). Acta Cryst. 19, 155-157]. The mol-ecule is planar with approximate D(3h) point symmetry, yet it crystallizes in the chiral ortho-rhom-bic space group P2(1)2(1)2(1) with a three-dimensional hydrogen-bonding network containing infinite O-Hâ¯O-Hâ¯O-H chains.