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Water Mediated, Eco-friendly Enantioselective Synthesis of Indole Substituted N-heterocyclic Compounds via Friedel-Crafts Alkylation

[ Vol. 14 , Issue. 5 ]

Author(s):

Madhu Bandi* and Ch.Venkata Ramana Reddy   Pages 372 - 380 ( 9 )

Abstract:


Background: Among the nitrogen heterocycles, quinolones and their derivatives represent the most important class of organic scaffolds that attract the interest of both medicinal and synthetic chemists. And these molecules possess a large number of biological and pharmacological properties. Here, we have synthesized 3-(1-(1H-indol-3-yl)-3-oxo-3-phenylpropyl)-4-hydroxy-1-methylquinolin- 2(1H)-ones 5 in presence of L-proline through the intermediacy of 4-hydroxy-1-methyl-3-(3-oxo-3- phenylprop-1-en-1-yl)quinolin-2(1H)-one 3.

Methods: All the compounds 5(aa-ce) have been synthesized in step-wise, one-pot with sequential addition and one-pot process with all substrates present from the outset methods under green conditions. The structure of the product was established based on its spectral properties IR, 1H- NMR, 13C-NMR and Mass.

Results: In this work we describe the synthesis of 3-(1-(1H-indol-3-yl)-3-oxo-3-phenylpropyl)-4- hydroxy-1-methylquinolin-2(1H)-ones 5(aa-ce) by condensation of 4-hydroxy-1-methyl-2-oxo-1,2- dihydroquinoline-3-carbaldehyde 1, with acetophenone 2(a-c) and indole 4(a-e) in the presence of L-proline and water.

Conclusion: We have synthesized new series of indole substituted N-heterocyclic chalcones via Friedel-Crafts alkylation under green condition. The syntheses are water mediated and eco-friendly involving easy workup: moreover they gave high yields without the need of costly catalyst and column chromatography.

Keywords:

Chalcones, Friedel-Crafts alkylation, L-proline, orixiarine, sodium dodecyl sulfate (SDS).

Affiliation:

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad (T.S), 500 085, Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad (T.S), 500 085

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