EventsThe 25th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-25-11673 (registering DOI)
This submission belongs to the session S1. General Organic Synthesis of the event The 25th International Electronic Conference on Synthetic Organic Chemistry
Published date
13 Nov, 2021
Academic Editor
author-avatarJulio A. Seijas
Citation
Didier Villemin, Salima Dib-Benzerjeb, Bachir Mostefa-Kara, Nathalie Bar, Study of Diels-Alder Reactions of Purpurogallin Tetra-Acetate with Various Dienophiles, in Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry, 15 November–30 November 2021, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-25-11673
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Study of Diels-Alder Reactions of Purpurogallin Tetra-Acetate with Various Dienophiles

Salima Dib-Benzerjeb 1
Bachir Mostefa-Kara 1
Didier Villemin 2
Nathalie Bar 3
1. Laboratoire de Catalyse Et Synthèse en Chimie Organique, Faculté des Sciences, Université de Tlemcen, BP 119, 13000, Tlemcen, Algeria
2. Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN et Université de Caen Normandie, 14050 Caen, France, France
3. Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN et Université de Caen Normandie, 14050 Caen, France
Abstract

Purpurogallin (1,7,8,9-Tetrahydroxy-2H-benzo[7]annulen-2-one) is a benzotropolone having a dienic system and is known to inhibits TLR1/TLR2 activation pathway. We have recently described the easy green synthesis of purpurogallin from pyrogallol catalyzed by a copper complex or by vegetable oxidases.

The purpurogalline was acetylated and the tetraacetate derivative thus obtained was engaged in a Diels Alder reaction with various dienophiles (benzoquinone, maleic anhydride, ethylmaleimide, azodicarboxylate, etc.). The results obtained will be presented and discussed. Theoretical calculations using DFT have been performed.

Keywords
cycloaddition
Diels-Alder
tropolone
DFT
Manuscript
sciforum_053819.pdf
Oral Presentation
SCIDA.pptx
Poster
SCIDA.pdf
SCIDA.pdf
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