Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives

被引:56
作者
Banik, BK [1 ]
Zegrocka, O [1 ]
Banik, I [1 ]
Hackfeld, L [1 ]
Becker, FF [1 ]
机构
[1] Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Expt Pathol Sect, Houston, TX 77030 USA
关键词
samarium metal; reduction; radical; secondary amines;
D O I
10.1016/S0040-4039(99)01395-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Samarium metal induced iodine-catalyzed reduction of the imines towards the synthesis of secondary amines was investigated. The imines derived from aromatic amines produced monoamines whereas imines from arylalkyl amines gave diamines in good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6731 / 6734
页数:4
相关论文
共 13 条
[1]   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
[2]   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
[3]   New synthesis and reactions of [Sm(OTf)2(DME)2], a salt-free samarium(II) triflate [J].
Collin, J ;
Giuseppone, N ;
Machrouhi, F ;
Namy, JL ;
Nief, F .
TETRAHEDRON LETTERS, 1999, 40 (16) :3161-3164
[4]   A ROUTE TO VICINAL DIAMINES FROM THE SAMARIUM(II) IODIDE-MEDIATED COUPLING OF ALDIMINES [J].
ENHOLM, EJ ;
FORBES, DC ;
HOLUB, DP .
SYNTHETIC COMMUNICATIONS, 1990, 20 (07) :981-987
[5]   REDUCTION WITH ORGANIC SELENIUM-COMPOUNDS .2. REDUCTION OF SCHIFF-BASES WITH SELENOPHENOL REDUCTIVE ALKYLATION OF AMINES WITH CARBONYL-COMPOUNDS [J].
FUJIMORI, K ;
YOSHIMOTO, H ;
OAE, S .
TETRAHEDRON LETTERS, 1980, 21 (35) :3385-3388
[6]   Facile reduction of azides to the corresponding amines with metallic samarium and catalytic amount of iodine [J].
Huang, Y ;
Zhang, YM ;
Wang, YL .
TETRAHEDRON LETTERS, 1997, 38 (06) :1065-1066
[7]   A mild, convenient, and inexpensive method for converting imines into amines: Tin-catalyzed reduction with polymethylhydrosiloxane (PMHS) [J].
Lopez, RM ;
Fu, GC .
TETRAHEDRON, 1997, 53 (48) :16349-16354
[8]   Samarium ion-promoted cross-aldol reactions and tandem aldol/Evans-Tishchenko reactions [J].
Lu, L ;
Chang, HY ;
Fang, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :843-853
[9]   Samarium diiodide nickel diiodide an efficient system for homo and heterocoupling reactions of imines [J].
Machrouhi, F ;
Namy, JL .
TETRAHEDRON LETTERS, 1999, 40 (07) :1315-1318
[10]  
MATSUMURA Y, 1982, TETRAHEDRON LETT, V23, P1932