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One-pot synthesis of pyrrolooxazoles from pyrrolyl acetylenic ketones and natural aldehydes

Denis Nikolaevich Tomilin 1
Denis Nikolaevich Tomilin
, 
Sophia Aleksandrovna Stepanova 1, 2
Sophia Aleksandrovna Stepanova
,  , 
Ludmila Andreevna Oparina 1
Ludmila Andreevna Oparina
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
1 A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
2 Irkutsk National Research Technical University, 664074 Irkutsk, Russian Federation
10.71267/mencom.7571
Published 2025-01-24
Communication , Volume 35, Issue 1, 14-17
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Tomilin D. N. et al. One-pot synthesis of pyrrolooxazoles from pyrrolyl acetylenic ketones and natural aldehydes // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 14-17.
GOST all authors (up to 50) Copy
Tomilin D. N., Stepanova S. A., Sobenina L. N., Oparina L. A., Ushakov I. A., Trofimov B. A. One-pot synthesis of pyrrolooxazoles from pyrrolyl acetylenic ketones and natural aldehydes // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 14-17.
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TY - JOUR
DO - 10.71267/mencom.7571
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7571
TI - One-pot synthesis of pyrrolooxazoles from pyrrolyl acetylenic ketones and natural aldehydes
T2 - Mendeleev Communications
AU - Tomilin, Denis Nikolaevich
AU - Stepanova, Sophia Aleksandrovna
AU - Sobenina, Lyubov Nikolaevna
AU - Oparina, Ludmila Andreevna
AU - Ushakov, Igor Alekseevich
AU - Trofimov, Boris Aleksandrovich
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 14-17
IS - 1
VL - 35
ER -
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@article{2025_Tomilin,
author = {Denis Nikolaevich Tomilin and Sophia Aleksandrovna Stepanova and Lyubov Nikolaevna Sobenina and Ludmila Andreevna Oparina and Igor Alekseevich Ushakov and Boris Aleksandrovich Trofimov},
title = {One-pot synthesis of pyrrolooxazoles from pyrrolyl acetylenic ketones and natural aldehydes},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7571},
number = {1},
pages = {14--17},
doi = {10.71267/mencom.7571}
}
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Tomilin, Denis Nikolaevich, et al. “One-pot synthesis of pyrrolooxazoles from pyrrolyl acetylenic ketones and natural aldehydes.” Mendeleev Communications, vol. 35, no. 1, Jan. 2025, pp. 14-17. https://mendcomm.colab.ws/publications/10.71267/mencom.7571.

Keywords

2-c]oxazoles
3
4
4-di- and 3
5-trimethoxybenzaldehydes
cinnamaldehyde
citral
cyclization.
natural aldehydes
pyrrolo[1
pyrrolyl acetylenic ketones
syringaldehyde
vanillin

Abstract

Natural aldehydes and some of their derivatives undergo base-catalyzed [3 + 2]-cyclization with pyrrolyl acetylenic ketones in a click-like manner (Et2O, KOH, room temperature) to afford pyrrolo[1,2-c]oxazoles in up to 77% yield, a novel family of pharmaceutically prospective compounds.

Funders

Ministry of Education and Science of the Russian Federation
122041100031-5

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