Synthesis of indolylquinoline and acridone alkalaids- A green approach

We have described the total syntheses of quinoline alkaloids, which include indoloquinoline, naphthyridine alkaloids like perlolidine and acridone alkaloids. Synthesis of 1-oxo-1,2,3,4-tetrahydrocarbazole was achieved with good yield using conventional and microwave procedure (unconventional energy). The utility of indole-3-butanoic acid and ethyl 4-(1H-indol-3-yl)butanoate were studied by adopting various catalysts and solvents. As our major synthetic targets were the indoloquinoline alkaloids, we have used Vilsmeier Haack reaction to synthesis and Fischer-indole synthesis to synthesize 3-(2-(1H- indol-3-yl)ethyl)-2- chloroquinoline and 2,4-dihydroxy-3-(indol-2-)-yl-quinoline from ethyl 4-(1H-indol-3-yl)butanoate and 3-acyl-2,4-dihydroxy quinoline respectively. Our investigations on the Vilsmeier Haack reaction (conventional and microwave procedure) of 3-acyl-2,4-dihydroxy quinoline ended up with an intermediate 3-(3-chloroprop-2-ene-1-al)-2,4-dichloroquinoline. The synthetic utility 3-(3-chloroprop-2-ene-1-al)-2,4-dichloroquinoline towards the construction of acridone by using Wittig mechanism with ethyl 2- (triphenylphosphoranylidene was documented.

Autorentext

Dr. Nepolraj Amaladoss has got 10 years of research experience in synthetic organic chemistry and three years teaching experience in Organic chemistry for both under graduate and post graduate at Annai college of arts and science, Kumbakonam, india. He completed UG, PG and Doctoral studies GAC-Kumbakonam, filled of research synthesis of quinoline.