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.
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.
Tang
Qiang
Q
Key Laboratory of Green Chemistry and Technology of Ministry of Education at Sichuan University, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Zhang
Chao
C
Luo
Meiming
M
D000586:Amination; D000588:Amines / Q000138:chemical synthesis*; D006834:Hydrazines / Q000737:chemistry*; D006912:Hydroxyquinolines / Q000737:chemistry; D009281:Naphthalenes / Q000737:chemistry; D009284:Naphthols / Q000138:chemical synthesis / Q000737:chemistry*; D010659:Phenylhydrazines / Q000737:chemistry
D000588:Amines; D006834:Hydrazines; D006912:Hydroxyquinolines; D009281:Naphthalenes; D009284:Naphthols; D010659:Phenylhydrazines; C020628:4-methylphenylhydrazine