4965-30-4Relevant academic research and scientific papers
Nitrosation of phenolic substrates under mildly basic conditions: Selective preparation of p-quinone monooximes and their antiviral activities
Ishikawa, Tsutomu,Watanabe, Toshiko,Tanigawa, Hisashi,Saito, Tatsuru,Kotake, Ken-Ichiro,Ohashi, Yoshiaki,Ishii, Hisashi
, p. 2774 - 2779 (2007/10/03)
Nitrosation of 3-methoxyphenol and 1-naphthol were examined under both acidic (NaNO2-EtCO2H-H2O) and basic (i-AmNO2-K2CO3-DMF) conditions. Acidic nitrosations afforded ortho-directed products, whereas para-directed nitrosations were observed under basic conditions to yield p-quinone monooximes. The basic para-directed nitrosation was further examined using 15 phenols, two naphthols, and four phenolic heterocyclics. A one-pot operation of the basic nitrosation followed by methylation with dimethyl sulfate gave the corresponding methyl ethers in high yield. Two p-quinone monooximes derived from 3-methoxyphenol and 8-hydroxyquinoline showed a moderate activity against HSV-1, and the latter oxime was also effective against HSV-2. On the other hand, p-quinone monooximes derived from methyl salicylate, 1-naphthol, 7-hydroxy-2-methylbenzo[b]furan, and 8-hydroxycoumarin showed the comparable activity to that of DDI against HIV-1.
REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. VIII. THE ORIGIN OF THE OXYGEN ATOM OF THE HYDROXY GROUP IN THE PRODUCTS FROM THE HYDROXYLATION OF 1-NITRONAPHTHALENE WITH ALKALI AND MOLECULAR OXYGEN
Malykhin, E. V.,Shteingarts, V. D.
, p. 938 - 946 (2007/10/02)
In the reaction of 1-nitronaphthalene witk K(18)OH and (16)O2 in liquid ammonia 1-nitro-2- and 4-nitro-1-naphthols labeled with the (18)O isotope in the hydroxyl group are formed.The ratio of the isomers and the content of the (18)O isotope depend on the ratio of 1-nitronaphthalene and alkali, on the temperature, and on the presence of moisture in the ammonia.The amount of the (18)O isotope in the hydroxylation products indicates that in contrast to the analogous reaction of nitrobenzene and its derivatives the hydroxy function of the products in this case is formed not only from the alkali but also to a significant degree from the oxygen of the O2.
Light-Induced Self-Nitrosation of Polycyclic Phenols with Nitrosamine. Excited State Proton Transfer
Chow, Yuan L.,Wu, Zheng-Zhi
, p. 5260 - 5267 (2007/10/02)
Photoexcitation of polycyclic phenols in the presence of N-nitrosodimethylamine caused the self-nitrosation of the phenols to give 1,2- or 1,4-quinone monooximes.With use of naphthols as models, the key step of the photonitrosation was shown to be a dual sensitization process from the lowest singlet excited state of naphthols by proton transfer followed by energy migration within an exciplex to cause the known homolysis of the nitrosamine; it is assumed that the resulting radical species undergo nitrosation of naphtholates.The crucial requirement of the excited state proton transfer (ESPT) reaction is established by quenching of the photonitrosation by general bases, such as water and TEA, with quenching rate constants close to those of naphthol fluorescence by these bases.
REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. I. SUBSTITUTION OF HYDROGEN ATOM BY HYDROXY GROUP IN AROMATIC NITRO COMPOUNDS BY THE ACTION OF POTASSIUM HYDROXIDE AND OXYGEN
Malykhin, E.V.,Shtark, A.A.,Shteingarts, V.D.
, p. 1661 - 1666 (2007/10/02)
The reaction of nitrobenzene and 1-nitro- and 1,5- and 1,8-dinitronaphthalenes with potassium hydroxide and oxygen in liquid ammonia at -33 deg C gives nitrophenols and nitro- and dinitronaphthols respectively, corresponding to substitution of the hydrogen atom of the hydroxy group at the ortho and para positions to the nitro group. 4-Nitro-3-hydroxybiphenyl was obtained from 4-nitrobiphenyl under analogous conditions.The reaction of 1-nitronaphthalene with potassium hydroxide and oxygen at -70 deg C is characterized by exclusive ortho entry of the hydroxy group in relation to the nitro group.
