Iron catalyzed site selective and chelation assisted C-H functionalization in 8-amidoquinolines is achieved. The remote C5-benzoxylation with benzoyl peroxide produced a variety of potentially bioactive 8-arylcarboxamido-5-benzoyloxy quinoline derivatives. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on carboxamide and acyl peroxide in addition to tolerance of halo-substitutions on either of the aryls. The reaction is additive, silver free and proceeds without the exclusion of air or moisture.
Water-mediated one-pot Mannich type condensation of dibenzo[b,d]furan-2-ol with different amines resulted in a large library of novel 2,3-dihydro-1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazine derivatives in moderate to excellent yields. The ortho-aminomethylation of the dibenzofuranols proceeded smoothly in the presence of various aromatic/aliphatic amines and paraformaldehyde, followed by cyclization. All the newly synthesized tetracyclic 2,3-dihydro-1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazine derivatives were chemically characterized and screened for their cytotoxicity activity by cell viability assay (MTT test) against three human cancer cell lines and antibacterial activity by determining the minimum inhibitory concentration (MIC) against four bacterial strains. Among all the derivatives, MCV-24 showed promising anticancer activity by inhibiting the cell proliferation of an ovarian cancer cell line (SKOV3) with an IC value at 7.5 µM, whereas MCV-24 to MCV-30 derivatives showed moderate activity against a lung cancer cell line (A549) with an IC value ranging from 11 to 15.9 µM. Besides MCV-29, -30, and -31 also exhibited broad-spectrum antibacterial activity. Among all new compounds, MCV-24-30 showed promising anticancer and MCV-29-31 antibacterial activity.
Oxygenative cleavage of an inert CAr–NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is achieved through an efficient, catalyst free, one step synthesis of 8-benzyloxy, 7-aminoquinoline directly from 8-aminoquinoline in water at room temperature.
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