Events The 20th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session c. Symposium on Microwave Assisted Synthesis of the event The 20th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2016

Citation

Ines Mancini, Andrea Defant, Michele Demozzi, Efficient TBD-Catalyzed Synthesis of Capsaicin-like Molecules , in Proceedings of The 20th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2016, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-20-c003

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Efficient TBD-Catalyzed Synthesis of Capsaicin-like Molecules

Andrea Defant ¹

Michele Demozzi ¹

Ines Mancini ²

1. Laboratory of Bioorganic Chemistry, Department of Physics, University of Trento, Via Sommarive 14, 38123 Trento, Italy

2. Laboratory of Bioorganic Chemistry, Department of Physics, University of Trento, Via Sommarive 14, 38123 Trento, Italy, Italy

Abstract

Capsaicin (= (E)-N-(4-hydroxy‐3‐methoxybenzyl)‐8‐methyl‐6‐nonenamide), the natural compound responsible for the spicy flavor in pepper fruits, has shown antioxidant and weight-reductive properties, cardiovascular benefits, anti-carcinogenic activity and recently pain relief effects. Studies on a series of synthetic capsacinoids indicated that the length of alkyl chain affected piquancy, with the possibility of obtaining non‐pungent capsaicin analogues with interesting bioactivieties.¹

We report here on a new efficient procedure for the synthesis of capsaicin analogues, based on the aminolysis of vanillylamine with methyl esters showing structural changes in alkyl chain, catalyzed by the inexpensive and non-toxic triazabicyclo[4.4.0]dec‐5‐ene (TBD).² The procedure is improved by microwave irradiation, which allows to carry out the reaction under solvent-free conditions and to obtain high yields of products. This is an effective and fast procedure for the access to a wide library of capsaicinoids for further biological evaluations, as well as for a large-scale production.

References

M.L.Reyes‐Escogido, E. G.Gonzalez‐Mondragon, E.Vazquez‐Tzompantzi, Molecules 2011,16,1253.
C. Sabot, K. A. Kumar, S. Meunier, C. Mioskowski, Tetrahedron Lett. 2007, 48, 3863.

Keywords

capsacinois

MW-assisted synthesis

TBD-catalyst

Manuscript

Capsaicin manuscript.pdf

Poster

Mancini_ID sciforum-009184.pdf

Synthesis of triazoloquinazolinone derivatives employing Silica-based sulfonic acid (MCM- 41-SO3H): A mild, reusable and highly efficient heterogeneous catalyst

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