Indium metal as a reducing agent in organic synthesis

被引:166
作者
Pitts, MR [1 ]
Harrison, JR [1 ]
Moody, CJ [1 ]
机构
[1] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 09期
关键词
D O I
10.1039/b101712h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and alpha -oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.
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页码:955 / 977
页数:23
相关论文
共 187 条
[11]   The grignard'sche reaction. [J].
Baeyer, A .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1905, 38 :2759-2765
[12]  
BAILEY PS, 1973, ORG SYNTH, V5, P489
[13]   KINETICS AND MECHANISM OF BENZYLATION OF ANILINES [J].
BALLISTRERI, FP ;
MACCARONE, E ;
MAMO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (21) :3364-3367
[14]   A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine [J].
Banik, BK ;
Mukhopadhyay, C ;
Venkatraman, MS ;
Becker, FF .
TETRAHEDRON LETTERS, 1998, 39 (40) :7243-7246
[15]   Indium/ammonium chloride mediated selective reduction of aromatic nitro compounds: Practical synthesis of 6-aminochrysene [J].
Banik, BK ;
Suhendra, M ;
Banik, I ;
Becker, FF .
SYNTHETIC COMMUNICATIONS, 2000, 30 (20) :3745-3754
[16]  
BARON C, 1962, B SOC CHIM FR, P1113
[17]  
Baruah B, 1999, SYNLETT, P409
[18]   Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride [J].
Basu, MK ;
Becker, FF ;
Banik, BK .
TETRAHEDRON LETTERS, 2000, 41 (30) :5603-5606
[19]   Indolequinone antitumor agents:: Correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity [J].
Beall, HD ;
Winski, S ;
Swann, E ;
Hudnott, AR ;
Cotterill, AS ;
O'Sullivan, N ;
Green, SJ ;
Bien, R ;
Siegel, D ;
Ross, D ;
Moody, CJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4755-4766
[20]  
Beek HS, 2000, TETRAHEDRON LETT, V41, P8097