$$\hbox {FeCl}_{3}$$ FeCl 3 -catalyzed $$[3{+}3]$$ [ 3 + 3 ] annulation between 3-oxirane-indolin-2-ones and nitrones to construct spiro[1,4,2-dioxazinan]oxindoles

$$\hbox {FeCl}_{3}$$ FeCl 3 -catalyzed $$[3{+}3]$$ [ 3 + 3 ] annulation between... efficient synthesis for the construction of containing a spiro- quaternary carbon and multiple stereocenters spirooxindole heterocyclic compounds is a still demanding task. Notably, it is a rare synthetic method of substituted six-membered spirooxindoles from simple substrates and catalysts, which would further broaden the scope of spirooxindoles [7–10]. Therefore, further exploration of the scope of available spirooxindole cores remains elusive. The reactivity of nitrones has been widely investigated because they are very useful synthetic intermediates in Keywords FeCl · Annulation · Spirooxindole · Nitrone · medicinal chemistry [11]. Nitrone, as a typical 1,3-dipole, Ring expansion could react with alkenes [12–15], alkynes [16–20], and cyclo- propanes [21–25] to form heterocyclic compounds, which are important structural motifs found in a number of nat- Introduction ural products and biologically active compounds [26]. On the other hand, strained triatomic cyclics such as cyclo- The ubiquity of the spirooxindole heterocyclic compounds propanes, oxiranes, and aziridines have been widely explored in many natural products, pharmacological agents and agro- in constructing various cyclics [27–31]. Among them, the [3+3] cycloaddition of donor–acceptor cyclopropanes with Electronic supplementary material The online version of this nitrones, pioneered by Kerr’s group [32], is a consider- article (doi:10.1007/s11030-017-9741-z) contains supplementary able elegant approach. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Molecular Diversity Springer Journals

$$\hbox {FeCl}_{3}$$ FeCl 3 -catalyzed $$[3{+}3]$$ [ 3 + 3 ] annulation between 3-oxirane-indolin-2-ones and nitrones to construct spiro[1,4,2-dioxazinan]oxindoles

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Publisher
Springer International Publishing
Copyright
Copyright © 2017 by Springer International Publishing Switzerland
Subject
Life Sciences; Biochemistry, general; Organic Chemistry; Polymer Sciences; Pharmacy
ISSN
1381-1991
eISSN
1573-501X
D.O.I.
10.1007/s11030-017-9741-z
Publisher site
See Article on Publisher Site

Abstract

efficient synthesis for the construction of containing a spiro- quaternary carbon and multiple stereocenters spirooxindole heterocyclic compounds is a still demanding task. Notably, it is a rare synthetic method of substituted six-membered spirooxindoles from simple substrates and catalysts, which would further broaden the scope of spirooxindoles [7–10]. Therefore, further exploration of the scope of available spirooxindole cores remains elusive. The reactivity of nitrones has been widely investigated because they are very useful synthetic intermediates in Keywords FeCl · Annulation · Spirooxindole · Nitrone · medicinal chemistry [11]. Nitrone, as a typical 1,3-dipole, Ring expansion could react with alkenes [12–15], alkynes [16–20], and cyclo- propanes [21–25] to form heterocyclic compounds, which are important structural motifs found in a number of nat- Introduction ural products and biologically active compounds [26]. On the other hand, strained triatomic cyclics such as cyclo- The ubiquity of the spirooxindole heterocyclic compounds propanes, oxiranes, and aziridines have been widely explored in many natural products, pharmacological agents and agro- in constructing various cyclics [27–31]. Among them, the [3+3] cycloaddition of donor–acceptor cyclopropanes with Electronic supplementary material The online version of this nitrones, pioneered by Kerr’s group [32], is a consider- article (doi:10.1007/s11030-017-9741-z) contains supplementary able elegant approach.

Journal

Molecular DiversitySpringer Journals

Published: Apr 24, 2017

References

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