O -Vinylhydroxylamines for De Novo Pyrrole Synthesis
5 affiliations
- 1Department of Chemistry
- 2Rice University
- 3Enamine Ltd, Winston Churchill St. 78, 02094 Kyiv, Ukraine
- 4Institute of Functional Materials Chemistry, State Scientific Institution State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Ave., 60, 61072 Kharkiv, Ukraine
- 5Taras Shevchenko National University of Kyiv, Faculty of Chemistry, Volodymyrska, 60, 01601 Kyiv, Ukraine
Abstract
High Resolution Image Download MS PowerPoint Slide Regioselective access to electron-deficient and highly substituted pyrroles from simple building blocks remains challenging. Here we show that O -vinylhydroxylamines enable the de novo construction of pyrroles through an aza-Michael/oxaza-Cope [3,3]-sigmatropic rearrangement/aromatization cascade with activated alkynes. This one-pot transformation proceeds rapidly at room temperature using catalytic amounts of a mild organic base and furnishes dihydropyrrole hemiaminal intermediates that can be directly converted to pyrroles or selectively functionalized. The method accommodates a broad range of O -vinylhydroxylamines and activated alkyne partners and enables access to substitution patterns that previously required harsh conditions or hazardous acetylene-based methods. These results establish O -vinylhydroxylamines as versatile building blocks for the synthesis of highly functionalized pyrroles.
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BibTeX
@article{randolph2026vinylhydroxylamines,
title = {{O -Vinylhydroxylamines for De Novo Pyrrole Synthesis}},
author = {Charlotte Randolph and Oleksandr V. Buravov and Zachary Grimm and Pavel K. Mykhailiuk and László Kürti},
journal = {Journal of the American Chemical Society},
year = {2026},
month = may,
doi = {10.1021/jacs.6c06697},
url = {https://doi.org/10.1021/jacs.6c06697},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - O -Vinylhydroxylamines for De Novo Pyrrole Synthesis
AU - Charlotte Randolph
AU - Oleksandr V. Buravov
AU - Zachary Grimm
AU - Pavel K. Mykhailiuk
AU - László Kürti
PY - 2026
DA - 2026/05/23
JO - Journal of the American Chemical Society
DO - 10.1021/jacs.6c06697
UR - https://doi.org/10.1021/jacs.6c06697
AB - High Resolution Image Download MS PowerPoint Slide Regioselective access to electron-deficient and highly substituted pyrroles from simple building blocks remains challenging. Here we show that O -vinylhydroxylamines enable the de novo construction of pyrroles through an aza-Michael/oxaza-Cope [3,3]-sigmatropic rearrangement/aromatization cascade with activated alkynes. This one-pot transformation proceeds rapidly at room temperature using catalytic amounts of a mild organic base and furnishes dihydropyrrole hemiaminal intermediates that can be directly converted to pyrroles or selectively functionalized. The method accommodates a broad range of O -vinylhydroxylamines and activated alkyne partners and enables access to substitution patterns that previously required harsh conditions or hazardous acetylene-based methods. These results establish O -vinylhydroxylamines as versatile building blocks for the synthesis of highly functionalized pyrroles.
SN - 0002-7863
SN - 1520-5126
SN - 1943-2984
ER -