Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system

被引:34
作者
Iranpoor, Nasser [1 ]
Firouzabadi, Habib
Nowrouzi, Najmeh
Firouzabadi, Dena
机构
[1] Shiraz Univ, Dept Chem, Shiraz 71454, Iran
[2] Shiraz Med Sci Univ, Fac Pharm, Shiraz, Iran
关键词
triphenylphosphine; silver nitrate; nitration; aromatic amines; NITRIC-ACID; TRIFLUOROACETIC-ANHYDRIDE; REGIOSELECTIVE NITRATION; TRIMETHYLSILYL-ETHERS; THIOLS; ALCOHOLS; CONVERSION; TRIPHENYLPHOSPHINE/2,3-DICHLORO-5,6-DICYANOBENZOQUINONE; THIOCYANATES; NITROSATION;
D O I
10.1016/j.tetlet.2006.07.054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of PPh3/Br-2/AgNO3 provides a new reagent system for the novel and highly chemoselective nitration of aromatic amines under mild reaction conditions. (c) 2006 Published by Elsevier Ltd.
引用
收藏
页码:6879 / 6881
页数:3
相关论文
共 29 条
[1]   A fast and mild method for the nitration of aromatic rings [J].
Bak, RR ;
Smallridge, AJ .
TETRAHEDRON LETTERS, 2001, 42 (38) :6767-6769
[2]   Nitration of polyethersulfone by ammonium nitrate and trifluoroacetic anhydride [J].
Botvay, A ;
Máthé, A ;
Pöppl, L .
POLYMER, 1999, 40 (17) :4965-4970
[3]   AROMATIC NITRATION WITH NITRIC-ACID AND TRIFLUOROMETHANESULFONIC ACID [J].
COON, CL ;
BLUCHER, WG ;
HILL, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (25) :4243-4248
[4]   NITRATIONS AND OXIDATIONS WITH INORGANIC NITRATE SALTS IN TRIFLUOROACETIC-ANHYDRIDE [J].
CRIVELLO, JV .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (15) :3056-3060
[5]   Zeolite-mediated regioselective nitration of phenol in solid state [J].
Esakkidurai, T ;
Pitchumani, K .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 185 (1-2) :305-309
[6]  
FETSCHER CA, 1963, ORG SYNTH, P735
[7]   Dinitrogen tetroxide-impregnated charcoal (N2O4/charcoal):: Selective nitrosation of amines, amides, ureas, and thiols [J].
Iranpoor, N ;
Firouzabadi, H ;
Pourali, AR .
SYNTHETIC COMMUNICATIONS, 2005, 35 (11) :1517-1526
[8]   A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone(DDQ)/n-Bu4NN3 system [J].
Iranpoor, N ;
Firouzabadi, H ;
Akhlaghinia, B ;
Nowrouzi, N .
TETRAHEDRON LETTERS, 2004, 45 (16) :3291-3294
[9]   Conversion of alcohols, thiols, and trimethysilyl ethers to alkyl cyanides using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/n-Bu4NCN [J].
Iranpoor, N ;
Firouzabadi, H ;
Akhlaghinia, B ;
Nowrouzi, N .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2562-2564
[10]   Conversion of alcohols, thiols, carboxylic acids, trimethylsilyl ethers, and carboxylates to thiocyanates with triphenylphosphine/diethylazodicarboxylate/NH4SCN [J].
Iranpoor, N ;
Firouzabadi, H ;
Akhlaghinia, B ;
Azadi, R .
SYNTHESIS-STUTTGART, 2004, (01) :92-96