Synthesis of novel benzo naphtho naphthyridines from 2,4-dicloroquinolines

A schematic study on the condensation of 2,4-dichloroquinolines ( 1 ) with 1-naphthyamine ( 2 ) in the presence of CuI as a catalyst to functionalized mono ( 3 ) and di ( 4 ) substituted naphthylamino quinolines was described. Consequently, these mono- and di-substituted amines on polyphosphoric acid-catalyzed cyclization reaction with p-toluic acid and acetic acid to yield the linear benzob]naphtho2,1-g]1,8]naphthyridines ( 5 ) and angular benzob]naphtho2,1-h] naphthyridines ( 6 ) in good yields. In addition to descried the similar synthesis of benzog]naphtho 2,1-b]1,8]naphthyridines ( 12 ) and benzoh]naphtho2,1-g]1,8]naphthyridines ( 13 ) from 2,4-dichlorobenzoh]quinoline ( 8 ) with various anilines ( 9 ) through my intermediates ( 10 and 11 ).