O-Vinylhydroxylamines for De Novo Pyrrole Synthesis
Тип публікації :
Препринт
Дата випуску :
31 березня 2026 р.
Автор(и) :
Charlotte Randolph
Oleksandr V. Buravov
Zachary Grimm
Pavel K. Mykhailiuk
László Kürti
eKNUTSHIR URL :
Журнал :
ChemRxiv
Цитування :
[APA 7] Charlotte, R., Oleksandr, V. B., Zachary, G., Pavel, K. M., & László, K. (2026). O-Vinylhydroxylamines for De Novo Pyrrole Synthesis. ChemRxiv,. https://doi.org/10.26434/chemrxiv.15001468/v1
[ДСТУ] O-Vinylhydroxylamines for De Novo Pyrrole Synthesis / R. Charlotte та ін. ChemRxiv. 2026. DOI: 10.26434/chemrxiv.15001468/v1 (дата звернення: 11.09.2026).
Regiospecific 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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