Synthesis of new fluorine-containing dihydrobenzo[c]acridines from trifluoroacetyl dihydronaphthalene and substituted anilines

Preparation of α,β-unsaturated trifluoromethylketones and their application in the synthesis of heterocycles

“…146 In the reaction of 462 with various substituted anilines the formation of enaminoketones 463 is observed. Compounds 463 are cyclized to the target dihydrobenzo [c] …”

Synthesis of new trifluoromethyl-containing cycloalka[b]quinolines derivated from alkoxycycloalkenes

“…Secondly, the intramolecular cyclization reactions of 2-trifluoroacetyl-1-(arylamino)-cycloalkenes (3a-f and 4a-f) were carried out in polyphosphoric acid (PPA) in the absence of solvent according to the method described in our earlier work. 9,10 At first, PPA (P 2 O 5 + H 3 PO 4 )…”

“…Subsequently, an intramolecular cyclization reaction of these 3,4-dihydro-naphthylamines carried out in polyphosphoric acid and in the absence of solvent afforded the corresponding series of 7-trifluoromethyl-5,6-dihydrobenzo[c]acridines. 10 The present study presents a general method to regiospecifically synthesize β-enaminoketones 3 and 4 and trifluoromethyl-cycloalka[b]quinolines 5 and 6 from the reaction of cyclic β-methoxyvinyl trifluoromethyl ketones 1 (n = 1 and 3) with six substituted anilines 2 (Scheme 1). Although many methods for the synthesis of quinolines 5 and 6 have been published, none of them have employed the strategy adopted in this study.…”

Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

“…One of the most satisfactory methods for introducing a CF 3 group into heterocycles is via the trifluoromethylated building block approach. 12,[15][16][17][18][19][20][21][22][23][24][25][26][27][28] The trifluoroacetylation of enol ethers or acetals provided, in one step and in good yields, β-alkoxyvinyl trifluoromethyl ketones 1 which proved to be useful building blocks for the synthesis of many series of heterocyclic compounds. 16,20,[22][23][24][25][26][27][28][29] Of no less importance, it is also well known that enaminocarbonyl compounds represent versatile synthetic precursors, which combine the ambident nucleophilicity of enamines with the ambident electrophilicity of enones, presenting three nucleophilic and two electrophilic sites.…”