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

被引:42
作者
Tang, Qiang [1 ]
Zhang, Chao [1 ]
Luo, Meiming [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
关键词
D O I
10.1021/ja711153b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:5840 / +
页数:3
相关论文
共 31 条
[1]   The NiCl2•2H2O-Li-Arene (cat.) combination as reducing system, part 6 -: Reduction of hydrazines, azo and azoxy compounds, and amine N-oxides with the NiCl2•2H2O-Li-DTBB (cat.) combination [J].
Alonso, F ;
Radivoy, G ;
Yus, M .
TETRAHEDRON, 2000, 56 (44) :8673-8678
[2]   ON THE REACTION OF BETA-NAPHTHOL WITH N,N-DIMETHYLHYDRAZINE - A NEW RADICAL AMINATION PROCESS [J].
BARTON, DHR ;
LEGRENEUR, S ;
MOTHERWELL, WB .
TETRAHEDRON LETTERS, 1983, 24 (15) :1601-1604
[3]  
BIN DL, 1978, SYNTHESIS-STUTTGART, P23
[4]   SYNTHESIS OF OPTICALLY-ACTIVE 2,2'-DIHALO-1,1'-BINAPHTHYLS VIA STABLE DIAZONIUM SALTS [J].
BROWN, KJ ;
BERRY, MS ;
MURDOCH, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4345-4349
[5]  
DARKE NL, 1942, ORG REACTIONS, V1, P105
[6]   LITHIUM-AMMONIA CLEAVAGE OF THE N-N BOND IN N-(METHOXYCARBONYL)-ACETYLHYDRAZINES AND N-ACETYLHYDRAZINES [J].
DENMARK, SE ;
NICAISE, O ;
EDWARDS, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6219-6223
[7]   Trifluoroacetyl-activated nitrogen-nitrogen bond cleavage of hydrazines by samarium(II) iodide [J].
Ding, H ;
Friestad, GK .
ORGANIC LETTERS, 2004, 6 (04) :637-640
[8]   Efficient asymmetric synthesis of α-trifluoromethyl-substituted primary amines via nucleophilic 1,2-addition to trifluoroacetaldehyde SAMP- or RAMP-hydrazone [J].
Enders, D ;
Funabiki, K .
ORGANIC LETTERS, 2001, 3 (10) :1575-1577
[9]   NEAR-INFRARED ABSORBING DYES [J].
FABIAN, J ;
NAKAZUMI, H ;
MATSUOKA, M .
CHEMICAL REVIEWS, 1992, 92 (06) :1197-1226
[10]  
Fernández R, 2000, ANGEW CHEM INT EDIT, V39, P2893, DOI 10.1002/1521-3773(20000818)39:16<2893::AID-ANIE2893>3.0.CO