One‐pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad
Elena Yu Schmidt
1
,
N. V. Semenova
1
,
Evgeniya E. Ivanova
1
,
Igor A. Ushakov
1
,
Ivan A Bidusenko
1
,
A. S. Bobkov
1, 2
,
Publication type: Journal Article
Publication date: 2024-11-04
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
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.
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Total citations:
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Citations from 2024:
3
(100%)
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Schmidt E. Yu. et al. One‐pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad // Advanced Synthesis and Catalysis. 2024. Vol. 367. No. 2. e202400953
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Schmidt E. Yu., Semenova N. V., Ivanova E. E., Ushakov I. A., Bidusenko I. A., Bobkov A. S., Vitkovskaya N., Trofimov B. A. One‐pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad // Advanced Synthesis and Catalysis. 2024. Vol. 367. No. 2. e202400953
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TY - JOUR
DO - 10.1002/adsc.202400953
UR - https://onlinelibrary.wiley.com/doi/10.1002/adsc.202400953
TI - One‐pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad
T2 - Advanced Synthesis and Catalysis
AU - Schmidt, Elena Yu
AU - Semenova, N. V.
AU - Ivanova, Evgeniya E.
AU - Ushakov, Igor A.
AU - Bidusenko, Ivan A
AU - Bobkov, A. S.
AU - Vitkovskaya, Nadezhda
AU - Trofimov, B. A.
PY - 2024
DA - 2024/11/04
PB - Wiley
IS - 2
VL - 367
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2024_Schmidt,
author = {Elena Yu Schmidt and N. V. Semenova and Evgeniya E. Ivanova and Igor A. Ushakov and Ivan A Bidusenko and A. S. Bobkov and Nadezhda Vitkovskaya and B. A. Trofimov},
title = {One‐pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad},
journal = {Advanced Synthesis and Catalysis},
year = {2024},
volume = {367},
publisher = {Wiley},
month = {nov},
url = {https://onlinelibrary.wiley.com/doi/10.1002/adsc.202400953},
number = {2},
pages = {e202400953},
doi = {10.1002/adsc.202400953}
}