Synthesis of Spirocyclic Pyrrolizidineoxyindoles with a Furotropylidene Fragment by 1,3-Dipolar Cycloaddition

被引：4
|
作者：
Tkachuk, A. V. [1 ]
Kurbatov, S. V. [1 ]
Burov, O. N. [1 ]
Kletskii, M. E. [1 ]
Morozov, P. G. [1 ]
Minkin, V. I. [1 ]
机构：
[1] Southern Fed Univ, Rostov Na Donu 344090, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2014年 / 50卷 / 01期
基金：
俄罗斯基础研究基金会;
关键词：
azomethine ylide; furotropone; isatin; spirooxyindole; spiropyrrolizidine; 1,3-dipolar cycloaddition; DFT (B3LYP/6-31G**); nucleophilic substitution; REGIOSELECTIVE SYNTHESIS; HETEROCYCLIC-COMPOUNDS; UNSATURATED ALDEHYDES; VINYL ETHERS; KETONES; ACETALS;
D O I：
10.1007/s10593-014-1444-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 1,3-dipolar cycloaddition of the unstabilized azomethine ylides generated in situ from isatin and proline to the endocyclic C = C bond of the tropylidene ring is absolutely regio- and diastereoselective. The local electrophilicity of the dipolarophile and the local nucleophilicity of the azomethine ylide calculated by the B3LYP/6-31G** method are useful tools for predicting the regioselectivity of cycloaddition. The structure and the three-dimensional structure of the synthesized spiropyrrolizidineoxyindoles were established by correlation NMR spectroscopy and X-ray structural analysis.
引用
收藏
页码：26 / 34
页数：9
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