One‐Pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad
Abstract Pharmaceutically prospective 2‐substituted‐4,5‐dimethyloxazoles are synthesized in 16–58% yield via cascade assembly of one molecule of primary amide with two molecules of acetylene gas in the KOH/MeOH/DMSO catalytic triad (90 °C, 2 h). This self‐organization of oxazoles demonstrates unexpected successful competition with the alkaline hydrolysis of amides. The mechanism involving amide N ‐vinylation, enamine‐imine isomerization, imine ethynylation and intramolecular O ‐vinylation cascade sequence has been deduced and supported by quantum‐chemical calculations using the B2PLYP−D3/6‐311+G**//B3LYP/6‐31+G*+IEF PCM (B3LYP/6‐31+G*) approach.
Authors
- N. M. Vitkovskaya (ORCID: https://orcid.org/0000-0002-3001-082X)
- Elena Yu. Schmidt (ORCID: https://orcid.org/0000-0002-0188-3015)
- Nadezhda V. Semenova (ORCID: https://orcid.org/0000-0002-2937-970X)
- Ivan A. Bidusenko (ORCID: https://orcid.org/0000-0003-0783-6233)
- Б. А. Трофимов (ORCID: https://orcid.org/0000-0002-0430-3215)
- Igor Ushakov (ORCID: https://orcid.org/0000-0002-6988-9261)
- Alexander S. Bobkov (ORCID: https://orcid.org/0000-0001-8901-3577)
- Evgeniya Ivanova
Institutions
- A.E. Favorsky Irkutsk Institute of Chemistry (RU)
- Irkutsk State University (RU)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1002/adsc.202400953
- Citations
- 4
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Analytical Center for the Government of the Russian Federation
- Russian Science Foundation
- Ministry of Science and Higher Education of the Russian Federation