3560-30-3Relevant articles and documents
Regiodivergent Aromatic Electrophilic Substitution Using Nitrosoarenes in Hexafluoroisopropanol: A Gateway for Diarylamines and p-Iminoquinones Synthesis
Pradhan, Suman,Roy, Sourav,Ghosh, Soumen,Chatterjee, Indranil
supporting information, p. 4294 - 4301 (2019/08/20)
A metal-free aromatic electrophilic substitution reaction using nitrosoarenes as the electrophile in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is reported. HFIP activates nitrosoarene towards the electrophilic C?H amination followed by a concomitant N?O bo
Direct ortho-Selective Amination of 2-Naphthol and Its Analogues with Hydrazines
Jia, Lei,Tang, Qiang,Luo, Meiming,Zeng, Xiaoming
, p. 5082 - 5091 (2018/05/15)
Described herein is a regioselective ortho-amination of 2-naphthol and its analogues with substituted hydrazines. It provides a direct methodology for the synthesis of N-arylaminated naphthol derivatives without the formation of related 1,1′-biaryl-2,2′-diamine or carbazole byproducts. Specifically, using N,N-disubstituted hydrazine precursors, N-unsubstituted ortho-aminated derivatives and related secondary amines can be formed in ethylene glycol in moderate to excellent yields. Variation of substrates to N,N′-diarylhydrazines and N-methyl-N,N′-diarylhydrazines led to N-aryl-1-amino-2-naphthol compounds. It is noted that biologically interesting indazole motifs can be facilely created by the reaction of N,N′-dialkylhydrazines with 2-naphthols. These ortho-amination reactions have the advantage of one-pot operation without the use of transition metal catalysts.
Reaction of Triphenylphosphine with Copper Complexes derived from 2-Nitrosophenols (1,2-Quinone Mono-oximes)
Buckley, Robert G.,Charalambous, John,Kensett, Malcolm J.,McPartlin, Mary,Mukerjee, Deepak,et al.
, p. 693 - 697 (2007/10/02)
Reaction of triphenylphosphine with the copper(II) complexes of 5-methoxy-2-nitrosophenol, 4-methyl-2-nitrosophenol, 1-nitroso-2-naphthol, and 2-nitroso-1-naphthol involves deoxygenation of one of the ligands to give 2-amino-7-methoxy-3H-phenoxazin-3-one, 4-methyl-2-aminophenol, 1-amino-2-naphthol, and 2-amino-N4-(1-hydroxy-2-naphthyl)-1,4-naphthoquinone 4-imine respectively as the major organic products.In all cases reduction of the metal occurs to give a complex of type Cu(qo)(PPh3)2 (qoH = nitrosophenol).The reactions are rationalised in terms of nitrene intermediacy.An X-ray diffraction study of Cu(qo)(PPh3)2 (qoH = 1-nitroso-2-naphthol) has been undertaken.
