SYNTHESIS OF TETRAHYDROISOQUINOLINES VIA INTRAMOLECULAR ELECTROPHILIC AROMATIC-SUBSTITUTION REACTIONS OF PUMMERER-DERIVED SUBSTITUTED N-BENZYL-N-TOSYL-ALPHA-AMINOTHIONIUM IONS

被引：30

作者：

CRAIG, D ^{[1
]}

DANIELS, K ^{[1
]}

MACKENZIE, AR ^{[1
]}

机构：

[1] PFIZER LTD,CENT RES,SANDWICH CT13 9NJ,KENT,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 37期

关键词：

D O I：

10.1016/S0040-4020(01)80458-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition to (phenylsulfinyl)ethene 1 of substituted benzylic amines 2 followed by N-tosylation gives substituted N-benzyl-N-tosyl-2-amino-1-(phenylsulfinyl)ethanes 3. Treatment of 3 with trimethylsilyl trifluoromethanesulfonate-Hunig's base gives 4-(phenylsulfenyl)-N-tosyl-1,2,3,4-tetrahydroisoquinolines 4 via presumed intramolecular trapping of Pummerer-derived substituted N-benzyl-N-tosyl-alpha-aminothionium ions 5.

引用

页码：7803 / 7816

页数：14

共 25 条

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