
TY  - JOUR
A1  - Prager, RH 
A1  - Were, ST 
T1  - The synthesis of perloline, 6-(3,4-Dimethoxyphenyl)-5-hydroxy-5,6-dihydrobenzo[c]-[2,7]naphthyridin-4(3H)-one
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 7
SP  - 1441
EP  - 1453
KW  - 
UR  - https://doi.org/10.1071/CH9831441 
N2  - Dehydroperloline is obtained in high overall yield by an intramolecular cyclization of the benzyne generated from 4-(2-bromophenyl)-N-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (21), by use of lithium hexamethyldisilazide. A benzyne intermediate has not been established. The pyridinone (21) was prepared in three steps from 2-[1-(2-bromophenyl)ethylidene]malononitrile. Dehydroperloline was smoothly reduced by sodium bis(methoxyethoxy)aluminium hydride to perloline, isolated as its hydrochloride. 
ER  -

