Trifluoromethyl substituted Delta(3)-imidazolines: Synthesis and reactivity

被引：8

作者：

Derstine, CW ^{[1
]}

Smith, DN ^{[1
]}

Katzenellenbogen, JA ^{[1
]}

机构：

[1] UNIV ILLINOIS,DEPT CHEM,URBANA,IL 61801

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(97)00934-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the preparation of various 4-trifluoromethyl-substituted Delta(3)-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from alpha-silylimines and trifluoroacetonitrile by a 3+2 cycloaddition, and they can be hydrolyzed in weak acid to trifluoromethyl ketones. Additionally, we have identified several ring-opened compounds which result from treatment of the imidazolines with acid or base. Attempts to alkylate the imidazolines led to ring-opened products, so that the alkylation sequence ultimately produced N-alkylated amino acid-derived trifluoromethyl ketones. (C) 1997 Elsevier Science Ltd.

引用

页码：4359 / 4362

页数：4

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