Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems

被引:25
作者
Bahajaj, AA [1 ]
Vernon, JM [1 ]
Wilson, GD [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 12期
关键词
D O I
10.1039/b009316p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrido[2',3':3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine derivatives are obtained by heating in polyphosphoric acid (PPA) appropriate hydroxy lactam precursors derived from pyridine-2,3-dicarboximides. The stereoselectivity of ring closure is rationalised by considering the development of A(1,3) strain in the cyclisation step from N-acyliminium ion intermediates.
引用
收藏
页码:1446 / 1451
页数:6
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