том 367 издание 2 номер публикации e202400953

One‐pot Synthesis of 2‐Substituted‐4,5‐dimethyloxazoles from Amides and Acetylene Gas in the KOH/MeOH/DMSO Catalytic Triad

Тип публикацииJournal Article
Дата публикации2024-11-04
SCImago Q1
WOS Q1
БС1
SJR0.704
CiteScore8
Impact factor4
ISSN16154150, 16154169
Краткое описание

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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Russian Chemical Reviews
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Organic and Biomolecular Chemistry
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Journal of Organic Chemistry
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Mendeleev Communications
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
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Royal Society of Chemistry (RSC)
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American Chemical Society (ACS)
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OOO Zhurnal "Mendeleevskie Soobshcheniya"
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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}
}
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