OXIDATION REACTIONS OF 2'-FUNCTIONALIZED 3-ARYLTETRAHYDROQUINOLINES AND 3,4-DIHYDROISOQUINOLINES

被引：13
|
作者：
SOTOMAYOR, N [1 ]
DOMINGUEZ, E [1 ]
LETE, E [1 ]
机构：
[1] UNIV BASQUE COUNTRY, FAC CIENCIAS, DEPT QUIM ORGAN, E-48080 BILBAO, SPAIN
来源：
TETRAHEDRON | 1995年 / 51卷 / 46期
关键词：
D O I：
10.1016/0040-4020(95)00827-U
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several 2'-functionalized 3-arylisoquinolines in different oxidation stages have been prepared. Fremy's salt or I-2/NaAcO oxidation of 2'-functionalized 3-aryltetrahydroisoquinolines always stops at the 3,4-dihydroisquinoline stage; however, better yields and shorter reaction Limes are obtained with iodine. Air/KOH/DMSO oxidation of 3,4-dihydroisoquinolines furnished the aromatic derivatives with concomitant cleavage of the TBDPS group. While 3-arylisoquinolin-1-(2H)-ones are obtained by air oxidation of 3,4-dihydroisquinolinium salts, the use of DDQ in dioxane resulted in a selective dehydrogenation to the corresponding N-substituted isoquinolinium salts.
引用
收藏
页码：12721 / 12730
页数：10
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