REDUCTION OF ISOQUINOLINE AND PYRIDINE-CONTAINING HETEROCYCLES WITH LITHIUM TRIETHYLBOROHYDRIDE (SUPER-HYDRIDE(R))

被引:32
作者
BLOUGH, BE [1 ]
CARROLL, FI [1 ]
机构
[1] RES TRIANGLE INST,POB 12194,RES TRIANGLE PK,NC 27709
关键词
D O I
10.1016/S0040-4039(00)79297-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isoquinolines, quinoline and pyridines are effectively reduced to 1,2,3,4-tetrahydroisoquinolines, 1,2,3,4-tetrahydroquinolines and piperidines respectively with lithium triethylborohydride (Super-Hydride(R)). The mechanism of the reduction was explored by reduction of isoquinoline and pyridine with lithium triethylborodeuteride (Super-Deuteride(R)).
引用
收藏
页码:7239 / 7242
页数:4
相关论文
共 7 条
[1]   SYNTHESIS OF 3-HALOMETHYL-2,3,4,5-TETRAHYDRO-2,5-METHANO-1H-2-BENZAZEPINES AND THEIR REARRANGEMENT TO 4-HALO-1,2,3,4,5,6-HEXAHYDRO-2,6-METHANO-2-BENZAZOCINES [J].
BLOUGH, BE ;
MASCARELLA, SW ;
ROTHMAN, RB ;
CARROLL, FI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :758-760
[2]   SELECTIVE REDUCTIONS .26. LITHIUM TRIETHYLBOROHYDRIDE AS AN EXCEPTIONALLY POWERFUL AND SELECTIVE REDUCING AGENT IN ORGANIC-SYNTHESIS - EXPLORATION OF THE REACTIONS WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS [J].
BROWN, HC ;
KIM, SC ;
KRISHNAMURTHY, S .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (01) :1-12
[3]   REDUCTIVE ALKYLATION OF ISOQUINOLINE [J].
GARSIDE, P ;
RITCHIE, AC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (23) :2140-&
[4]  
GRIBBLE GW, 1975, SYNTHESIS-STUTTGART, P650
[5]   A NEW SYNTHESIS OF 4-SUBSTITUTED ISOQUINOLINES [J].
MINTER, DE ;
RE, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2653-2655
[6]   THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].
STILLE, JK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :508-523
[7]   NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING .2. GRIGNARD COUPLING OF HETEROCYCLIC-COMPOUNDS [J].
TAMAO, K ;
KODAMA, S ;
NAKAJIMA, I ;
KUMADA, M ;
MINATO, A ;
SUZUKI, K .
TETRAHEDRON, 1982, 38 (22) :3347-3354