SYNTHESIS OF QUINOLINE DERIVATIVES BY REACTION OF DIMETHYL(2R,3S,4R)-2-PHENYL-4-(PHENYLAMINO)-1,3,4-TRIHYDROQUINOLINE-2,3-DICARBOXYLATE WITH SOME AMINES

In this work, quinoline derivatives were synthesized from reaction of aniline, benzylaldehyde and dimethylacetylene dicarboxylate (DMAD) in sequent steps to provide quinoline derivative dimethyl (2R, 3S, 4R)-2-phenyl-4-(phenylamino)-1, 3, 4-trihydroquinoline-2,3-dicarboxylate (12). Compound (12), was reacted with some amines such as  hydrazine hydrate, urea, thiourea, ethylenediamine, diaminopropane, dinitrophenylhydrazine and o-phenylenediamine to give (3aS,9R,9aS)-2-amino-3a-phenyl-9-(phenylamino)-4,9,9a-trihydro-pyrrolo[3,4-b]quinoline-1,3-dione (13),  (3aR) – 1,3 – dioxo – 3a-phenyl-9-(phenylamino)-4,9,9a-trihydro-pyrrolo[3,4-b]quinoline-2-carboxamide (14), (3aS)-1,3-dioxo-3a-phenyl-9-(phenylamino)-4,9,9a-trihydro-pyrrolo[3,4-b] quinoline – 2-carbothioamide (15),  6a-phenyl-12-(phenylamino)-2,3,4,5,7,12,12a-heptahydro-[1,4]diazocino[6,7-b]quinoline-1,6-dione (16),  (7aS)-7a-phenyl-13-(phenylamino)-2,3,4,5,6,8,13,13a-octahydro-[1,5]diazonino[7,8-b]quinoline-1,7-dione (17),  2-((2,4-dinitrophenyl)amino)-9-(phenylamino)- 4, 9, 9 a – trihydro-pyrrolo [3,4-b] quinoline-1,3-dione (18), and 2-(2-aminophenyl)-6a-phenyl-12-(phenylamino)-2, 4,5,7,12,12a-hexahydro-diazocino[3,4-b]quinoline-1,6- dione (19) respectively. Reaction of (12) sodium metal gave methyl 3-oxo-2-phenyl-5-(phenylamino)-1,2, 4,5-tetrahydro- benzo[b]azepine-4-carboxylate(20). These reactions were carried out with different solvents like acetonitrile, ethanol, and chloroform providing good yields of the new heterocyclic compounds (13-20) of quinoline derivatives. The identification of the compounds(13-20) were based on spectroscopic analysis such as IR, UV, ¹H-NMR, ¹³C-NMR, and the microanalysis of the elements (CHN) data.