Cyclizations of substituted benzylidene-3-alkenylamines:: Synthesis of the tricyclic core of the martinellines

被引:82
作者
Frank, KE [1 ]
Aubé, J [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1021/jo990843c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The martinellines (1 and 2) are natural products that possess both interesting biological activity and chemical structure. During the investigation of a hetero Diels-Alder route to these molecules, alternate Lewis acid-dependent cyclizations of (2'-amino-N'-tert-butoxycarbonyl-5'-chlorobenzylidene)-3-butenylamine (10) were observed. The reaction of a variety of imines with TMSOTf or TiCl4 led to the formation of different heterocycles including iminodibenzo[b,f][1,5]diazocines, hexahydropyrido[1,2-c]quinazolin-6-ones, tetrahydropyrrolo[1,2-c]quinazolin-5-ones, 2-arylpiperidines, and 2-arylpyrrolidines. Tetrahydropyrrolo[1,2-c]quinazolin-5-one 54, obtained via this new methodology, was used as an intermediate in the synthesis of the tricyclic ring system (65) of the martinellines.
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页码:655 / 666
页数:12
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