Novel Synthesis, Molecular Structure, and Theoretical Studies of Dispiro Compounds via Pseudo-eight-component Reaction

Nourallah Hazeri; Mojtaba Lashkari; Santiago García-Granda; Laura Torre-Fernández

doi:10.1071/CH13713

RESEARCH ARTICLE

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Novel Synthesis, Molecular Structure, and Theoretical Studies of Dispiro Compounds via Pseudo-eight-component Reaction

Nourallah Hazeri ^A ^C , Mojtaba Lashkari ^A , Santiago García-Granda ^B and Laura Torre-Fernández ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, PO Box 98135-674 Zahedan, Iran.

^B Department of Physical and Analytical Chemistry, University of Oviedo–Centro de Investigación en Nanomateriales y Nanotecnología (CINN), c/ Julián Clavería, 8, 33006 Oviedo, Spain.

^C Corresponding author. Email: nhazeri@chem.usb.ac.ir

Australian Journal of Chemistry 67(11) 1656-1665 https://doi.org/10.1071/CH13713
Submitted: 2 January 2014 Accepted: 2 March 2014 Published: 8 May 2014

Abstract

We have developed a diastereoselective synthesis of dispiro compounds through a one-pot domino pseudo-eight-component reaction of amines, aldehydes, and Meldrum’s acid. This method resulted in the generation of complex products with four stereocentres and involves formation of 10 new bonds. Quantum mechanical calculations were undertaken in order to determine the stability of the eight diastereomer structures of compound 4a. The crystal structure of 4k was determined by X-ray crystallography. Reaction mechanism can proceed through Knoevenagel, Aldol condensations, Diels-Alder cycloaddition, and Michael addition.

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Novel Synthesis, Molecular Structure, and Theoretical Studies of Dispiro Compounds via Pseudo-eight-component Reaction

Abstract

References

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