J. Am. Chem. Soc., ASAP Article - A New Method for N−N Bond Cleavage of N,N-Disubstituted Hydrazines to Secondary Amines and Direct Ortho Amination of Naphthol and Its Analogues
Qiang Tang, Chao Zhang, and Meiming Luo*Key Laboratory of Green Chemistry and Technology of Ministry of Education at Sichuan University, College of Chemistry, Sichuan University, Chengdu 610064, PR China
[email]luomm@scu.edu.cn[/email]
Received December 16, 2007
Abstract:
An unexpected reaction of N,N-disubstituted hydrazine with naphthol and its analogues under simply thermal conditions has been disclosed. 2-Naphthol reacted with various N,N-disubstituted hydrazines under argon to afford 1-amino-2-naphthol and the corresponding secondary amines in excellent yields. Ortho amination of 2-naphthols, hydroxyquinoline, and naphthalenamine occurred when they reacted with N-methyl-N-phenylhydrazine.
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