52486-77-8Relevant academic research and scientific papers
Quinoline alkaloids: Synthesis of pyrano[2,3,-b]quinolines, khaplofoline, lunacrine, and demethoxylunacrine
Sekar,Prasad
, p. 294 - 296 (2007/10/03)
Polyphosphoric acid (PPA)-catalyzed cyclization of 2-ono-3- vinylquinolinecarboxylic acid (1) yielded 3,4-dihydro-2,2-dimethyl-2H- pyrano[2,3-b]quinoline (4). The same reaction of 4-methoxy-2-oxo-3- vinylquinolinecarboxylic acid (1g) afforded 4-methoxy-2,2-dimethylpyrano[2,3- b]-quinoline (4g), which on hydrolysis with ethanolic hydrochloric acid gave khaplofoline (5). The Prevost reaction of 4-methoxy-3-prenylquinolin-2-one (6) using I2/HgO in acetic acid yielded 4-methoxy-2-isopropylfuro[2,3- b]quinoline (7). Compound 7 on reduction with H2/Pd-C followed by N- methylation and de-O-methylation afforded lunacrine (10a). A similar reaction sequence on 6b gave demethoxylunacrine (10b).
SYNTHESIS OF 2-ISOPROPYLFURO(2,3-b)QUINOLINES-A NEW SYNTHESIS OF (+/-)-LUNACRINE, (+/-)-LUNASINE AND (+/-)-DEMETHOXYLUNACRINE
Ramesh, M.,Mohan, P.S.,Shanmugam, P.
, p. 3431 - 3436 (2007/10/02)
A new and convenient synthesis of 2-isopropylfuro(2,3-b)quinolines (4) from 3-(3-methylbut-1-enyl)-2-quinolones (2) is described.A neat synthesis of the alkaloids (+/-)-lunacrine (1a), (+/-)-lunasine (12a) and (+/-)-demethoxylunacrine (1b) is also reported.
