REDUCIVE AMINATION OF PHTHALALDEHYDE BY TETRACARBONYLHYDRIDOFERRATE - SYNTHESIS OF 2-ARYLISOINDOLES

被引:38
作者
WATANABE, Y
SHIM, SC
UCHIDA, H
MITSUDO, T
TAKEGAMI, Y
机构
[1] Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University, Sakyo-ku, Kyoto
关键词
D O I
10.1016/0040-4020(79)85039-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phthalaldehyde reacted with primary amines in the presence of tetracarbonylhydridoferrate under mild conditions to give 2-substituted isoindoles and/or isoindolines in good to excellent yields. Aliphatic amines gave selectively the isoindolines but aromatic amines had a great tendency to the isoindoles. 2-(2-Tolyl)-, 2-(4-tolyl)-, 2-(4-methoxyphenyl)-, 2-(3-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-(3,4-dichlorophenyl)-isoindole were prepared by this method. © 1979.
引用
收藏
页码:1433 / 1436
页数:4
相关论文
共 25 条
[1]   ISOINDOLE [J].
BONNETT, R ;
BROWN, RFC ;
SMITH, RG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (13) :1432-1436
[2]   ISOINDOLE [J].
BONNETT, R ;
BROWN, RFC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :393-&
[3]   SYNTHESIS OF ISOINDOLE BY RETRO-DIELS-ALDER REACTION [J].
BORNSTEI.J ;
SHIELDS, JE ;
REMY, DE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (20) :1149-&
[4]  
BORNSTEIN J, 1974, TETRAHEDRON LETT, P4247
[5]   ALKYLATION OF AMMONIA AND ITS DERIVATIVES BY ORTHO XYLYLENEDIHALIDES [J].
DAUTH, C .
JOURNAL FUR PRAKTISCHE CHEMIE, 1971, 313 (04) :686-&
[6]   REACTIONS OF PHTHALALDEHYDE WITH AMMONIA AND AMINES [J].
DOMINH, T ;
JOHNSON, AL ;
JONES, JE ;
SENISE, PP .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) :4217-4221
[7]   REACTIVE INTERMEDIATES .26. FLASH VACUUM PYROLYSIS OF PHENYL-SUBSTITUTED 1,2,4-TRIAZOLES - NEW SYNTHESIS OF ISOINDOLES [J].
GILCHRIST, TL ;
REES, CW ;
THOMAS, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (01) :12-18
[8]   BENZOHETEROCYCLES VIA ARYNE C-C CYCLIZATION - 2-METHYLISOINDOLE [J].
JAQUES, B ;
WALLACE, RG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :397-&
[9]  
KREHER R, 1973, TETRAHEDRON LETT, P1911
[10]  
KREHER R, 1974, Z NATURFORSCH B, VB 29, P683