- Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols
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Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc)2/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)2/Cs2CO3 system and benzoic acid as an additive. These ligand-free conditions and “open-flask” chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.
- Siva Reddy,Ranjith Reddy,Nageswar Rao,Jaladanki, Chaitanya K.,Bharatam, Prasad V.,Lam, Patrick Y. S.,Das, Parthasarathi
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supporting information
p. 801 - 806
(2017/02/05)
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- RESEARCH IN THE CHEMISTRY OF HETEROCYCLIC QUINONE IMINES. 11. EFFECT OF BENZANNELATION ON THE OXIDATIVE CYCLIZATION OF DIARYLAMINO-N-ARYL-1,4-BENZOQUINONE MONOIMINES TO PHENAZINONE DERIVATIVES
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2,5-Diarylamino-N-α(β)-naphthyl-1,4-benzoquinone monoimines undergo oxidative cyclization to give benzannelated phenazinone derivatives.The effect of an N-aryl fragment on the ease of cyclization decreases in the order N-β-naphthyl > N-α-naphthyl > N-phenyl. 2-Arylamino-N-phenyl-1,4-naphthoquinone monoimines do not undergo oxidative cyclization to phenazinones.
- Afanas'eva, G. B.,Tsoi, E. V.
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p. 616 - 620
(2007/10/02)
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- Method of inhibiting leukotriene biosynthesis by oral administration of p-aminophenols or derivatives thereof
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A method is provided for inhibiting leukotriene biosynthesis and thus treating asthma, psoriasis or inflammation by oral administration of p-aminophenols having the structure STR1 wherein m is 0 to 5; X is CH or N; R1 and R2 may be the same or different and are H, lower alkyl, aryl, hydroxy, hydroxyalkyleneoxy, alkylthio, alkoxy, alkanoyloxy, aryloxy, halo, carboxy, alkoxycarbonyl or amido; R3 is H, lower alkyl, alkanoyl or aroyl; and R4 is H, lower alkyl, benzoyl or alkanoyl, and including acid-addition salts thereof, with the proviso that when R4 is benzoyl, R2 is other than H.
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- Quinoline compounds and compositions thereof
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p-Aminophenols are provided having the structure STR1 wherein m is 0 to 5; X is CH or N; R1 and R2 may be the same or different and are H, lower alkyl, aryl, hydroxy, hydroxyalkyleneoxy, alkylthio, alkoxy, alkanoyloxy, aryloxy, halo, carboxy, alkoxycarbonyl or amido; R3 is H, lower alkyl, alkanoyl or aroyl; and R4 is H, lower alkyl or alkanoyl, and including acid-addition salts thereof, with the proviso that when X is CH, m is 0 and R1 is H, and when R4 is H, R2 is other than alkoxy, H or hydroxy, and when R4 is benzoyl, R2 is other than H. These compounds together with the compounds defined in the above proviso are useful as inhibitors of leukotriene production and as such are useful as antiallergy, anti-inflammatory and anti-psoriatic agents.
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