A new route to 2-aryl-4-quinolones via palladium-catalyzed carbonylative coupling of o-iodoanilines with terminal arylacetylenes

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

“…Thus, as early as in 1991, Torii and co-workers reported this type of 225 In the presence of 5 mol % of palladium catalyst and under 20 bar of CO at 120°C, 2-substituted 1,4-dihydro-4-oxo-quinolines were produced in good yields (Scheme 75). Shortly after, Kalinin and co-workers reported the same process by using 10 mol % of PdCl 2 (DPPF) in Et 2 NH under 20 bar of CO at 120°C, 226 which was later applied by Haddad et al in the synthesis of BILN 2061 derivatives (Scheme 75a). 227 Alternatively, the palladiumcatalyzed reaction of 3-(2-haloarylamino)prop-2-enoates leads to quinoline derivatives.…”

Palladium-Catalyzed Carbonylative Synthesis of Six-Membered Heterocycles from Aryl Halides

“…Two years later, Kalinin and coworkers synthesized 2-substituted quinolin-4ones from 2-iodoanilines and terminal alkynes (Scheme 27) [55]. They used 5 mol % PdCl 2 (PPh 3 ) 2 as the catalyst and diethylamine as the solvent.…”

Use of Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dihydroquinolinones of Pharmaceutical Interest From 2′‐Aminochalcones

“…They display significant cytotoxicity against a panel of human tumor cell lines and also have high activity toward multi‐drug resistant KB‐VIN, and ovarian 1A9 cell lines. In addition, aza‐analogs of flavanones can also serve as valuable precursors for the synthesis of other pharmaceutical and active compounds; for example, those with potent antimitotic antitumor effects, such as 2‐aryl‐4‐quinolones derivatives and 4‐alcoxy‐2‐arylquinolines, which are often not readily accessible by other routes …”

“…The synthesis of these compounds has generated continuous interestb ecause of their wide range of biological activities, such as hypertensive, antibacterial, anti-inflammatory,a nd as anticancer and immunosuppressive agents. [1][2][3] They display significant cytotoxicity againstapanel of human tumor cell lines and also have high activity toward multi-drug resistant KB-VIN, and ovarian 1A9 cell lines.I na ddition, aza-analogs of flavanonesc an also serve as valuable precursors for the synthesis of other pharmaceutical and active compounds; [4,5] for example, those with potent antimitotic antitumor effects, [6] such as 2-aryl-4-quinolones derivatives [7] and 4-alcoxy-2-arylquinolines, [8] which are often not readily accessible by other routes. [9,10] The synthesis of 2,3-dihydro-4(1 H)-quinolinones is generally accomplished by the base or acid catalyzed intramolecular aza-Michael cyclization of substituted 2'-aminochalcones, through the nucleophilic attack of the amino group on the b-carbon of the enone function, which leads to the formation of six-membered heterocyclic systems( 6-endo-trigc yclization product) as predicted from Baldwin's rules (Scheme 1).…”