Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition

Yaghoub Sarrafi; Marzieh Sadatshahabi; Mahshid Hamzehloueian; Kamal Alimohammadi; Mahgol Tajbakhsh

doi:10.1055/s-0033-1338492

Synthesis, Table of Contents

Synthesis 2013; 45(16): 2294-2304
DOI: 10.1055/s-0033-1338492

paper

Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition

Authors

Yaghoub Sarrafi*

^aDepartment of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416, Iran Fax: +98(112)5342350 Email: ysarrafi@umz.ac.ir
Marzieh Sadatshahabi

^aDepartment of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416, Iran Fax: +98(112)5342350 Email: ysarrafi@umz.ac.ir
Mahshid Hamzehloueian

^bDepartment of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran
Kamal Alimohammadi

^cDepartment of Chemistry, Dr. Shariati Branch, Farhangian University, Sari, Iran
Mahgol Tajbakhsh

^aDepartment of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416, Iran Fax: +98(112)5342350 Email: ysarrafi@umz.ac.ir

Abstract

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Abstract

Dimethyl 2-(aryloxy)fumarates and dimethyl 2-(alkyl- or arylthio)fumarates are shown to be efficient dipolarophiles in 1,3-dipolar cycloaddition reaction with azomethine ylides, which are generated by the reaction of isatin with the secondary amino acids proline or sarcosine. In these reactions, dimethyl 2-(alkyl- or arylthio)fumarates afforded spirooxindolopyrrolizidines or -pyrrolidines in high yields with excellent regioselectivities, while dimethyl 2-(aryloxy)fumarates produced mixtures of regioisomers. DFT calculations at the B3LYP/6-31G(d,p) level were consistent with the observed results. Tri- and tetracyclic compounds were obtained through regio- and stereoselective intramolecular cycloaddition of O-vinylic salicylaldehyde with secondary amino acids.

Key words

2-(aryloxy)fumarates - 2-(alkyl- or arylthio)fumarates - azomethine ylides - spiro compounds - pyrrolizidines - pyrrolidines - DFT calculations

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References

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