Indium/ammonium chloride mediated selective reduction of aromatic nitro compounds: Practical synthesis of 6-aminochrysene

被引:46
作者
Banik, BK [1 ]
Suhendra, M [1 ]
Banik, I [1 ]
Becker, FF [1 ]
机构
[1] Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
关键词
D O I
10.1080/00397910008087002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of aromatic and heteroaromatic nitro compounds to the corresponding amino compounds was achieved by indium/ammonium chloride induced reaction in aqueous ethanol. This method was extended for the preparation of large quantities of 6-aminochrysene in excellent yield.
引用
收藏
页码:3745 / 3754
页数:10
相关论文
共 42 条
[1]   HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE [J].
ASKIN, D ;
WALLACE, MA ;
VACCA, JP ;
REAMER, RA ;
VOLANTE, RP ;
SHINKAI, I .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2771-2773
[2]   Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives [J].
Banik, BK ;
Zegrocka, O ;
Banik, I ;
Hackfeld, L ;
Becker, FF .
TETRAHEDRON LETTERS, 1999, 40 (37) :6731-6734
[3]   Microwave-induced organic reaction enhancement (MORE) chemistry. Part 13. Microwave-assisted rapid and simplified hydrogenation [J].
Banik, BK ;
Barakat, KJ ;
Wagle, DR ;
Manhas, MS ;
Bose, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :5746-5753
[4]   Benzylic oxidation by sodium bismuthate in acetic acid: A simple method for the synthesis of polycyclic aromatic ketones [J].
Banik, BK ;
Venkatraman, MS ;
Mukhopadhyay, C ;
Becker, FF .
TETRAHEDRON LETTERS, 1998, 39 (40) :7247-7250
[5]   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
[6]  
BANIK BK, 1999, 217 AM CHEM SOC NAT
[7]   Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of some chrysene derivatives [J].
Becker, FF ;
Banik, BK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (20) :2877-2880
[8]  
BOSE AK, 1993, SYNLETT, P575
[9]   Regioselectivity and diastereoselectivity in the indium-mediated homoallyl-cyclopropanation of dibenzylidene acetone (dba) [J].
Capps, SM ;
Lloyd-Jones, GC ;
Murray, M ;
Peakman, TM ;
Walsh, KE .
TETRAHEDRON LETTERS, 1998, 39 (18) :2853-2856
[10]   Stereoselective indium-mediated allylation of erythrulose derivatives in aqueous media [J].
Carda, M ;
Castillo, E ;
Rodriguez, S ;
Murga, J ;
Marco, JA .
TETRAHEDRON-ASYMMETRY, 1998, 9 (07) :1117-1120