- From paracetamol to rolipram and derivatives: Application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction
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A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization. Georg Thieme Verlag Stuttgart · New York.
- Schmidt, Bernd,Elizarov, Nelli,Berger, Rene,Petersen, Monibh.
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p. 1174 - 1180
(2013/06/05)
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- Synthesis, antimalarial activity, and structure-activity relationship of 7-(2-Phenoxyethoxy)-4(1H)-quinolones
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ICI 56,780 (5) displayed causal prophylactic and blood schizonticidal activity (ED50 = 0.05 mg/kg) in rodent malaria models but produced rapid acquisition of parasitological resistance in P. berghei infected mice. Herein we describe the synthesis of analogues of 5 with EC50 as low as 0.15 nM against multidrug resistant P. falciparum. Optimal activity with low cross-resistance indexes (RI) to atovaquone was achieved by introducing ortho-substituted aryl moieties at the 3-position of the 7-(2-phenoxyethoxy)- 4(1H)-quinolone core. (Figure presented
- Cross, R. Matthew,Namelikonda, Niranjan K.,Mutka, Tina S.,Luong, Lisa,Kyle, Dennis E.,Manetsch, Roman
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supporting information; experimental part
p. 8321 - 8327
(2012/02/04)
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- Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate)
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The reaction of anilides with phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroacetic acid (TFA), TFA-CHCl3, or hexafluoroisopropyl alcohol (HFIP) is described. When the acyl group of the anilide is highly electronegative, such as trifluoroacetyl, or the phenyl group is substituted with an electron-withdrawing group, the 4-iodophenyl group is transferred from PIFA to the amide nitrogen to afford acetyldiarylamines. On the other hand, when the acyl group contains an electron-donating function, such as 4-methoxyphenyl, or the phenyl group is substituted with an electron-donating group, a trifluoroacetoxy group is transferred to the para position of the anilide aromatic ring. This group is hydrolyzed during workup to produce the corresponding phenol.
- Itoh, Naoki,Sakamoto, Takeshi,Miyazawa, Etsuko,Kikugawa, Yasuo
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p. 7424 - 7428
(2007/10/03)
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- Production of benzophenone derivatives
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A method for producing a compound of the formula: wherein R is an acyl group or a silyl group, the rings A and B respectively may have one to four substituent(s), or a salt thereof, which comprists reacting a compound of the formula: wherein R has the same meaning as defined above, the ring A may have one to four substituents at the position(s) other than 2-position, or a salt thereof, with a compound of the formula: wherein Y is a hydroxyl group or a halogen atom, the ring B may have one to four substituent(s), or its salt, in the presence of a catalyst other than polyphosphonic acid. The method produces aminobenzophenone derivative of the formula (I) in a high purity, a high yield, with a conventional and commercially advantageous procedure.
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