Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2

“…This difference indicated that electrophilic substituents in the aromatic ring has a fundamental effect on the rate of deacylation. Compared with 2-chloro-N-arylacetamides bearing a benzene ring ( a The substrate(4 mmol) was treated with acetyl chloride (24 mmol) in the presence of 24 mmol K 2 CO 3 in acetone at room temperature b All products were identified by IR and 1 H NMR spectra c Yields refer to pure isolated products A facile and efficient method 81 [1][2][3][4][5][6][7][8][9][10][11][12], those with a aromatic heterocyclic ring (Table 8, entries 12-15) were, to some extent, less reactive and needed more than 3 h for completion of the reaction, but still afforded the corresponding products in excellent yields. We also found that both N-p-tolyl benzamide and N-benzyloxycarbonyl-benzamide could not be deacylated (not reported in this paper).…”

“…Hydrolysis of the acetyl amino group under basic (NaOH [1][2][3], KOH [4,5], etc.) or acidic (HCl [6,7], HBr [8], AcOH [9], etc.) conditions;…”

Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: synthetic outcomes and mechanistic considerations

“…8,9 Thanks to this, the area of quinolines and their functional derivatives polyfluorinated on a benzene ring has been opened for intensive elaboration. [9][10][11][12][13] We believed this methodology is possible to apply to N-acetyl derivatives of perfluoronaphthylamines for preparing their less fluorinated analogues unsubstituted ortho to an amino group as potential building blocks for polyfluoronaphthoazaheterocycles, some of which also can be highly biologically active (for example, by analogy with mono-and difluorobenzoquinolines 14 ).…”

“…Activated zinc (powder) was prepared by a technique, 22 Zn-Cu couple -by a technique. 12 Solvents and reagents were reagent quality.…”

A synthesis of ferrocenyl dihydrocoumarin and ferrocenyl dihydroquinolin-2(1H)-ones

“…It is possible that dihydrocoumarin, which attaches ferrocenyl, will increase its biological activity. 3,4-Dihydroquinolin-2(1H)-one can be prepared in good yield in the presence of acid catalyst by coupling anilines with cinnamic acids prior to hydroarylation [19][20] . The synthesis of dihydroquinolin with attached ferrocenyl has never been reported.…”