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

页码：26 / 34

页数：9

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