A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2+2] cycloaddition approach to carbocyclic spirooxindoles

被引：9
|
作者：
Brummond, Kay M. [1 ]
Osbourn, Joshua M. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 6卷
基金：
美国国家科学基金会;
关键词：
allene; propargylic acetate; spirooxindole; thermal [2+2] cycloaddition; thermal [3,3]-sigmatropic rearrangement; vinylidene indolin-2-one; CONSTRUCTION; VINYLALLENES; ALLENYNES; FACILE; CYCLODIMERIZATION; CYCLIZATIONS; INHIBITORS; MECHANISM;
D O I：
10.3762/bjoc.6.33
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of C3-carbocyclic spirooxindoles was realized by way of an intramolecular [2 + 2] cycloaddition reaction between a vinylidene indolin-2-one and an alkyne. The cycloaddition reaction occurs selectively with the distal double bond of the allene, is tolerant of a phenyl and trimethylsilyl group on the terminus of the alkyne, and can be used to access bicyclo[4.2.0]octadienes and bicyclo[5.2.0]nonadienes. The allene precursors are not observed, but are likely intermediates of an infrequently encountered thermal [3,3]-sigmatropic rearrangement of a propargylic acetate.
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页数：5
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