STRAIGHTFORWARD TRIFLUOROACYLATION OF OXAZOLES – SCALABLE, COST-EFFECTIVE WAY TOWARD DIVERSE 2-(TRIFLUOROACETYL)OXAZOLES

Authors

  • Vladyslav S. Savchenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094 Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601
  • Oleksandr V. Geraschenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Pavlo V. Khodakivskyi University of Missouri, W007 Locust St., Columbia, MO 65211
  • Tetiana V. Druzhenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Viktoria S. Moskvina Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601
  • Sergey V. Ryabukhin Enamine Ltd., 78 Winston Churchill St., Kyiv 02094 Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601 Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094
  • Dmitriy M. Volochnyuk Enamine Ltd., 78 Winston Churchill St., Kyiv 02094 Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601 Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094

DOI:

https://doi.org/10.1007/7653

Keywords:

oxazoles, trifluoroacetic anhydride, building blocks, direct trifluoroacylation, Henry reaction

Abstract

Feasible, scalable, and cost-effective method for the synthesis of low-molecular 2-(trifluoroacetyl)oxazoles from the corresponding oxazoles and trifluoroacetic anhydride was elaborated. The procedure was scaled up to 70 g of the desired ketones in a single run. Tolerance of the oxazole core to various functional group transformations was demonstrated. Thus, synthesis of various building blocks approved the possibility of using 2-(trifluoroacetyl)oxazoles as a starting materials for medicinal chemistry.

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers