REARRANGEMENT REACTIONS OF A REISSERT COMPOUND CHLOROHYDRIN

被引：10

作者：

KIRBY, GW ^{[1
]}

TAN, SL ^{[1
]}

UFF, BC ^{[1
]}

机构：

[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICESTERSHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 01期

关键词：

D O I：

10.1039/p19790000266

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Reissert compound, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline, reacted with hypochlorous acid to yield a crystalline chlorohydrin. Base-catalysed elimination of hydrogen chloride from this led to an array of rearranged products in a controlled manner. In this way, simple preparative routes to 1-benzoylamino-1-cyanoisochromene, 1-benzoyliminoisochromene (and thence isocoumarin), 1-ethoxy-4-formyl-3-phenylisoquinoline, and 1-ethoxy-3- phenylisoquinoline were devised. The mechanism of the consecutive rearrangements is discussed.

引用

页码：266 / 269

页数：4

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