Synthesis and further studies of chemical transformation of the 2-aryl-3-halogenoquinolin-4(1H)-one derivatives

Abstract

The C-3 brominated and iodinated derivatives were prepared from the corresponding 2-arylquinolin-4(1H)-ones and their NMe-4-oxo derivatives using pyridinium tribromide in acetic acid or iodine-Na 2 CO 3 mixture in THF. The results of further studies of chemical transformation of the prepared α-haloenones and preliminary antitumour activity of the 3-bromo NH-4-oxo and NMe-4-oxo derivatives are also described.

2,6,8‐Triaryl‐3‐iodoquinolin‐4(1H)‐ones as Substrates for the Synthesis of 2,3,6,8‐Tetraarylquinolin‐4(1H)‐ones and the 2‐Substituted 4,6,8‐Triaryl‐1H‐furo[3,2‐c]quinolines

“…Halogenation of quinolinone systems continues to attract considerable attention because of the profound effect; the introduction of a halogen atom into the heterocyclic ring can have on the physical, chemical, and biological properties of such systems. The electrophilic properties associated with iodine have been exploited in recent years to effect α‐halogenation of carbonyl compounds and their α,β‐unsaturated derivatives . Iodine and ceric ammonium nitrate (CAN: (NH 4 ) 2 Ce(NO 3 ) 6 ) in acetonitrile at 70–80°C afforded the 2‐aryl‐3‐iodoquinolin‐4(1 H )‐ones .…”

“…Iodine and ceric ammonium nitrate (CAN: (NH 4 ) 2 Ce(NO 3 ) 6 ) in acetonitrile at 70–80°C afforded the 2‐aryl‐3‐iodoquinolin‐4(1 H )‐ones . An iodine–Na 2 CO 3 mixture in THF at room temperature, on the other hand, was found to effect C‐3 iodination of the 2‐arylquinolin‐4(1 H )‐ones to yield the corresponding 2‐aryl‐3‐iodoquinolin‐4(1 H )‐ones in reasonable yield and high purity . The known 2,6,8‐triarylquinolin‐4(1 H )‐ones 1a , 1b , 1c , 1d , 1e , 1f , 1g , 1h were subjected to molecular iodine (1.5 equiv.)…”

“…Suzuki–Miyaura cross‐coupling of the N ‐alkyl 3‐halogenoquinolin‐4(1 H )‐ones with the arylboronic acids is well documented , and only limited examples that involve the cross‐coupling of the NH‐4‐oxo derivatives have been described in the literature . The 3‐iodo NH‐4‐oxo derivatives 2 were subjected to the Suzuki–Miyaura cross‐coupling with 4‐fluorophenylboronic acid or trans ‐(4‐fluorophenyl)vinyl boronic acid in the presence of dichlorobis(triphenyl)palladium(II)‐tricyclohexylphosphine [(PdCl 2 (PPh 3 ) 2 )‐PCy 3 ] catalyst complex and potassium carbonate as a base in dioxane–water mixture (4:1, v/v) under reflux.…”

“…α,β‐Unsaturated carbonyl compounds readily undergo halogenation to afford α‐haloenones, which provide an important functional group that facilitates metal‐catalyzed CC bond formation . Displacement of halogen atom/s on the aryl or heteroaryl moiety of halogenated heterocycles by metal catalysts provides an avenue for the installation of a wide range of carbon‐containing (alkyl, alkenyl, alkynyl, and aryl) and even heteroatom‐containing substituents.…”

Evaluation of the Antiangiogenic Effects of 2-Aryl-3-bromoquinolin-4(1H)-ones and a NCH3-4-oxo Derivative

“…4) This preliminary screening for the medicinal potential of 2-arylquinolin-4(1H)-ones provided a basis for further evaluation of antiangiogenic activities of some of the compounds that showed antitumor activity. Tumours require an efficient blood supply to survive and grow beyond a critical size.…”