Microwave-Assisted Synthesis and Odour Characteristics of Some New Isoxazolidines

  1. Akın SağırlıORCID Logo,
  2. Havva Acar,
  3. Hakan Özçal and
  4. Muhammet Büyükbayram

Submitting author affiliation: Bolu Abant Izzet Baysal University, Bolu, Turkey

Beilstein Arch. 2022, 20229. https://doi.org/10.3762/bxiv.2022.9.v1

Published 24 Feb 2022

  • Preprint

Abstract

We describe herein design and synthesis of new isoxazolidin-5-carboxylates by microwave-assisted 1,3-dipolar cycloadditions of aldonitrones, derived from five fragrant aldehydes, with methacrylate esters. The reaction proceeded regioselectively providing mostly endo- diastereomers and in some cases inseperable mixture of endo-exo products. The structures of target compounds were identified on the basis of IR, NMR and TOF-MS measurements. Besides, both aldonitrone and isoxazolidine derivatives was subjected to olfactory evaluation by an expert nose. Diverse fragrance notes were observed in each series of isoxazolidines bearing different groups from aldonitrons. However, their odour ranges were found as animalic, medical, waxy and ozonic undertones in common.

Keywords: Odour; isoxazolidine; methacrylate ester, microwave heating, aldonitrone

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Sağırlı, A.; Acar, H.; Özçal, H.; Büyükbayram, M. Beilstein Arch. 2022, 20229. doi:10.3762/bxiv.2022.9.v1

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