Synthesis of N-alkoxycarbonyl pyrroles from O-substituted carbamates A synthetically enabling pyrrole protection strategy

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Abstract

The condensation of readily available O-substituted carbamates with 2,5-dimethoxytetrahydrofuran gives N-alkoxycarbonyl pyrroles in a single step and in good yield. By this method, several common amine protecting groups can be introduced on the pyrrole nitrogen. With the exception of N-Boc, N-alkoxycarbonyl groups have seen only minimal use for protection of the pyrrole nitrogen to date. Here, we show that N-alkoxycarbonyl protection can endow pyrrole with distinct reactivity in comparison with N-sulfonyl protection, for example, in a pyrrole acylation protocol employing carboxylic acids with a sulfonic acid anhydride activator.
Original languageEnglish
Pages (from-to)13584–13589
Number of pages6
JournalJournal of Organic Chemistry
Volume88
Issue number19
Early online date6 Oct 2023
DOIs
Publication statusPublished - 6 Oct 2023

Funding

The authors thank EPSRC for a DTP PhD studentship to J.L.H. (EP/T518013/1). The authors acknowledge the Material and Chemical Characterization Facility (MC2) at the University of Bath (https://doi.org/10.15125/mx6j-3r54).

FundersFunder number
Engineering and Physical Sciences Research CouncilEP/T518013/1
University of Bath

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