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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Direct ortho-Selective Amination of 2-Naphthol and Its Analogues with Hydrazines
Lei Jia1, Qiang Tang1,2, Meiming Luo1
1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , PR China.
Abstract:
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.
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