One-pot multicomponent synthesis of some 5,6-dihydro-benzo[A]quinoline derivatives

Abstract EN

5-, 6Dihydrobenzo[ / j]quinoline derivatives 4a f and 5a-c were prepared via condensation of the corresponding arylidenes 2, with 1-tetralone in the presence of ammonium acetate and sodium meth oxide, respectively, following thermal, microwave and ultrasound methodologies.

The yields of 4a-f were moderate when the latter two methodologies used, but the products were pure.

Ultrasound and microwave irradiation methods were also used in the synthesis of 4-aryl-3-cyano-l, 2, 5, 6-tetrahydro-benzo [ / i] quinoline-2-ones (6a-e) and its analogues 7a,b.

The majority of compounds 4-7 were synthesized via one-pot multicomponent reactions of aldehydes, active cyan methylene compounds, 1-tetralone and ammonium acetate.

Attempts to cyclocondensation of the aminocyano derivative 4a, d with acetic anhydride in presence of cone.

H2S04 failed; instead the acetyl amino derivative 8 was isolated.

On the other hand, refluxing of 4d with form amide in DMF led to the formation of dihydrobenzo-pyrimidoquinoline 9 giving good yield.

All prepared condensates were structurally elucidated by various spectroscopic methods.

Screening of the potential cytotoxicity for compounds 4a-f on five cell lines, namely: colorectal carcinoma (HCT-116), Hepatocellular carcinoma (HEPG2), Human breast adenocarcinoma (MCF7), Cervix adenocarcinoma (HELA) and Glioblastoma (U251), did not show any cytotoxic activity.