SYNTHESIS OF HOMOALLYLAMINES BY THE ADDITION OF ALLYLIC INDIUM REAGENTS TO AZOMETHINES AND NITRILES

被引:41
作者
JIN, SJ [1 ]
ARAKI, S [1 ]
BUTSUGAN, Y [1 ]
机构
[1] NAGOYA INST TECHNOL, DEPT APPL CHEM, GOKISO CHO, SHOWA KU, NAGOYA, AICHI 466, JAPAN
关键词
D O I
10.1246/bcsj.66.1528
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Triallyldiindium trihalides and allylindate(I-)s reacted with N-benzylideneamines regioselectively at the C-3 carbon on the allyl group to give high yields of homoallylic secondary amines. Primary amines were obtained by the action of an excess of allylic indates on aromatic nitriles.
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页码:1528 / 1532
页数:5
相关论文
共 21 条
[1]   APPLICATION OF INDIUM ATE COMPLEXES TO SYNTHETIC CHEMISTRY - SELECTIVE CONJUGATE ADDITION TO ENONES AND COUPLING WITH ALLYLIC HALIDES [J].
ARAKI, S ;
SHIMIZU, T ;
JIN, SJ ;
BUTSUGAN, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (12) :824-825
[2]   ALLYLATION OF QUINONES BY ALLYLIC INDIUM REAGENTS [J].
ARAKI, S ;
KATSUMURA, N ;
BUTSUGAN, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 415 (01) :7-24
[3]   PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS [J].
ARAKI, S ;
SHIMIZU, T ;
JOHAR, PS ;
JIN, SJ ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2538-2542
[4]   INDIUM-INDUCED ALLYLATION OF ACID ANHYDRIDES - A FACILE SYNTHESIS OF ALLYLATED BUTENOLIDES AND PHTHALIDES [J].
ARAKI, S ;
KATSUMURA, N ;
ITO, H ;
BUTSUGAN, Y .
TETRAHEDRON LETTERS, 1989, 30 (12) :1581-1582
[5]   INDIUM IN ORGANIC-SYNTHESIS - INDIUM-MEDIATED ALLYLATION OF CARBONYL-COMPOUNDS [J].
ARAKI, S ;
ITO, H ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1831-1833
[6]   BETA-SUBSTITUTED ORGANO-LITHIUM COMPOUNDS - REACTION WITH ALKYL-HALIDES, DIMETHYL DISULFIDE, AND IMINES [J].
BARLUENGA, J ;
FANANAS, FJ ;
VILLAMANA, J ;
YUS, M .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) :1560-1564
[7]  
BENKESER RA, 1971, SYNTH-INT J METHODS, P347
[8]  
CHTARA RA, 1975, CR ACAD SCI C CHIM, V280, P1157
[9]   TERTIARY CARBINAMINES BY ADDITION OF ORGANOCERIUM REAGENTS TO NITRILES AND KETIMINES [J].
CIGANEK, E .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) :4521-4527
[10]   A CONVENIENT PREPARATION OF ALLYLLITHIUM [J].
EISCH, JJ ;
JACOBS, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (08) :2145-&