Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles

Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles DOI 10.1007/s10593-018-2280-4 Chemistry of Heterocyclic Compounds 2018, 54(4), 389–393 Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles 1 1 1 Serena Monticelli , Laura Castoldi , Saad Touqeer , 1 1 1 Margherita Miele , Ernst Urban , Vittorio Pace * Department of Pharmaceutical Chemistry, University of Vienna, 14 Althanstrasse, Vienna 1090, Austria; е-mail: vittorio.pace@univie.ac.at Published in Khimiya Geterotsiklicheskikh Soedinenii, Submitted March 15, 2018 2018, 54(0), 389–393 Accepted April 19, 2018 Spiro-epoxyoxindoles containing an unsubstituted methylene fragment in the oxirane ring are excellent building blocks in organic syn- thesis due to the high reactivity conferred by the three-membered oxygenated cycle. In this minireview, a concise survey of the methods of their synthesis and examples of reactivity with carbon and nitrogen nucleophiles is presented, with a particular focus on the stereo- chemical aspects. The review covers the literature for the last twenty years. Keywords: epoxides, isatins, spiro compounds, Friedel–Crafts reaction, nucleophilic addition. The 3,3'-disubstituted oxindole core is featured in several natural products and biologically active substances, thus representing an important target for the synthetic chemists. The corresponding spiro-epoxy derivatives induce a particular interest – they are characterized by the high reactivity conferred by the oxirane ring and can be http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry of Heterocyclic Compounds Springer Journals

Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles

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Publisher
Springer US
Copyright
Copyright © 2018 by Springer Science+Business Media, LLC, part of Springer Nature
Subject
Chemistry; Organic Chemistry; Pharmacy
ISSN
0009-3122
eISSN
1573-8353
D.O.I.
10.1007/s10593-018-2280-4
Publisher site
See Article on Publisher Site

Abstract

DOI 10.1007/s10593-018-2280-4 Chemistry of Heterocyclic Compounds 2018, 54(4), 389–393 Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles 1 1 1 Serena Monticelli , Laura Castoldi , Saad Touqeer , 1 1 1 Margherita Miele , Ernst Urban , Vittorio Pace * Department of Pharmaceutical Chemistry, University of Vienna, 14 Althanstrasse, Vienna 1090, Austria; е-mail: vittorio.pace@univie.ac.at Published in Khimiya Geterotsiklicheskikh Soedinenii, Submitted March 15, 2018 2018, 54(0), 389–393 Accepted April 19, 2018 Spiro-epoxyoxindoles containing an unsubstituted methylene fragment in the oxirane ring are excellent building blocks in organic syn- thesis due to the high reactivity conferred by the three-membered oxygenated cycle. In this minireview, a concise survey of the methods of their synthesis and examples of reactivity with carbon and nitrogen nucleophiles is presented, with a particular focus on the stereo- chemical aspects. The review covers the literature for the last twenty years. Keywords: epoxides, isatins, spiro compounds, Friedel–Crafts reaction, nucleophilic addition. The 3,3'-disubstituted oxindole core is featured in several natural products and biologically active substances, thus representing an important target for the synthetic chemists. The corresponding spiro-epoxy derivatives induce a particular interest – they are characterized by the high reactivity conferred by the oxirane ring and can be

Journal

Chemistry of Heterocyclic CompoundsSpringer Journals

Published: Jun 7, 2018

References

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