Selective reduction of barbituric acids using SmI2/H 2O: Synthesis, reactivity, and structural analysis of tetrahedral adducts

Michal Szostak; Brice Sautier; Malcolm Spain; Maike Behlendorf; David J. Procter

doi:10.1002/anie.201306484

Selective reduction of barbituric acids using SmI₂/H ₂O: Synthesis, reactivity, and structural analysis of tetrahedral adducts

Michal Szostak, Brice Sautier, Malcolm Spain, Maike Behlendorf, David J. Procter

Research output: Contribution to journal › Article › peer-review

64 Scopus citations

Abstract

Making a mark: Since the 1864 landmark discovery by Adolf von Baeyer, barbituric acids have played a prominent role in organic synthesis. Herein, the first chemoselective monoreduction of barbituric acids to the corresponding hemiaminals is described. The method delivers mono- and bicyclic hemiaminal products by a general single-electron-transfer polarity reversal mechanism.

Original language	English (US)
Pages (from-to)	12559-12563
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	48
DOIs	https://doi.org/10.1002/anie.201306484
State	Published - Nov 25 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

electron transfer
heterocycles
reductive coupling
samarium iodide
synthetic methods

Access to Document

10.1002/anie.201306484

Cite this

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