NOVEL SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF ORTHO-NITROSTYRENE DERIVATIVES

被引:55
作者
AKAZOME, M [1 ]
KONDO, T [1 ]
WATANABE, Y [1 ]
机构
[1] KYOTO UNIV, FAC ENGN, DEPT HYDROCARBON CHEM, SAKYO KU, KYOTO 60601, JAPAN
关键词
D O I
10.1246/cl.1992.769
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indole derivatives were readily prepared from the reductive N-heterocyclization of omicron-nitrostyrene derivatives in the presence of a catalytic amount of PdCl2(PPh3)2- SnCl2 under carbon monoxide pressure (20 kg/cm2) at 100-degrees-C for 16 h. With omicron-nitrostibene, 2-phenylindole was obtained in 75% yield.
引用
收藏
页码:769 / 772
页数:4
相关论文
共 18 条
[1]   PREPARATION + PROPERTIES OF IMIDO INTERMEDIATES ( IMIDOGENS ) [J].
ABRAMOVITCH, RA ;
DAVIS, BA .
CHEMICAL REVIEWS, 1964, 64 (02) :149-&
[2]   PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF N-(2-NITROBENZYLIDENE)AMINES INTO 2H-INDAZOLE DERIVATIVES [J].
AKAZOME, M ;
KONDO, T ;
WATANABE, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (20) :1466-1467
[3]   CATALYTIC REDUCTIVE CARBONYLATION OF AROMATIC NITRO-COMPOUNDS TO URETHANES PROMOTED BY SUPPORTED PALLADIUM ACTIVATED WITH 1,10-PHENANTHROLINE DERIVATIVES [J].
ALESSIO, E ;
MESTRONI, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 291 (01) :117-127
[4]   MODELING THE REDUCTION OF NITROBENZENE WITH [RU3(CO)12] AS A HOMOGENEOUS CATALYST - X-RAY STRUCTURES OF [RU3H(CO)10(PHNH)] AND [N(PPH3)2][RU3H(CO)9-(PHN)] [J].
BHADURI, S ;
KHWAJA, H ;
SAPRE, N ;
SHARMA, K ;
BASU, A ;
JONES, PG ;
CARPENTER, G .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1990, (04) :1313-1321
[5]   REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .14. DEOXYGENATION OF AROMATIC C-NITROSO-COMPOUNDS BY TRIETHYL PHOSPHITE AND TRIPHENYLPHOSPHINE - A NEW CYCLISATION REACTION [J].
BUNYAN, PJ ;
CADOGAN, JIG .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (JAN) :42-&
[6]   RUTHENIUM CARBONYL CATALYZED REDUCTIVE CARBONYLATION OF AROMATIC NITRO-COMPOUNDS - A SELECTIVE ROUTE TO CARBAMATES [J].
CENINI, S ;
CROTTI, C ;
PIZZOTTI, M ;
PORTA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1243-1250
[7]   CHEMOMETRIC OPTIMIZATION OF THE RUTHENIUM CARBONYL CATALYZED CYCLIZATION OF 2-NITROSTILBENE TO 2-PHENYLINDOLE [J].
CROTTI, C ;
CENINI, S ;
TODESCHINI, R ;
TOLLARI, S .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1991, 87 (17) :2811-2820
[8]   DEOXYGENATION REACTIONS OF ORTHO-NITROSTYRENES WITH CARBON-MONOXIDE CATALYZED BY METAL-CARBONYLS - A NEW ROUTE TO INDOLES [J].
CROTTI, C ;
CENINI, S ;
RINDONE, B ;
TOLLARI, S ;
DEMARTIN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :784-786
[9]   TRANSITION-METALS IN THE SYNTHESIS AND FUNCTIONALIZATION OF INDOLES [J].
HEGEDUS, LS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (09) :1113-1226