REACTIONS OF DIENE-CONJUGATED 1,3-DIPOLAR INTERMEDIATES - THE FORMATION OF CYCLOPROPA[C]ISOQUINOLINES FROM BENZONITRILE ORTHO-ALKENYLBENZYL YLIDES AND THEIR REARRANGEMENTS TO BENZAZEPINES

被引：13

作者：

MOTION, KR ^{[1
]}

ROBERTSON, IR ^{[1
]}

SHARP, JT ^{[1
]}

WALKINSHAW, MD ^{[1
]}

机构：

[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 13期

关键词：

D O I：

10.1039/p19920001709

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diene-conjugated nitrile ylides 19, generated by the 1,3-dehydrochlorination of imidoyl chlorides 18, cyclise at room temperature to give the cyclopropa[c]isoquinolines 21 in a stereospecific reaction. Thermal decomposition of the latter when R1 or R2 = H involves an equilibration between exo and endo isomers (Scheme 4) accompanied by a slower ring expansion to give 1H-2-benzazepines. In cases where neither R1 or R2 = H the thermal decomposition follows another path (Scheme 5) to give 5H-2-benzazepines. In contrast 32 and 38, the thiophene analogues of 19, do not give cyclopropa[b]thienopyridines 33 and 39, respectively but instead give the thienoazepines 35 and 41.

引用

页码：1709 / 1719

页数：11