Synthesis of 7- and 8-Functionalized 2-Aminophenoxazinones via Cyclocondensation of 2-Aminophenols

Jarosław M. Granda; Katarzyna Piekielska; Małgorzata Wąsińska; Natalia Kawecka; Mirosław Giurg

doi:10.1055/s-0034-1381011

Synthesis, Table of Contents

Synthesis 2015; 47(21): 3321-3332
DOI: 10.1055/s-0034-1381011

paper

Synthesis of 7- and 8-Functionalized 2-Aminophenoxazinones via Cyclocondensation of 2-Aminophenols

Jarosław M. Granda

,

Katarzyna Piekielska

,

Małgorzata Wąsińska

,

Natalia Kawecka

,

Mirosław Giurg*

Abstract

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Abstract

An efficient protocol for the synthesis of 7- and 8-functionalized 4- and 2-amino-3H-phenoxazin-3-ones and 2-amino-1H-phenoxazin-1-ones by oxidation of 2-aminophenols using hydrogen peroxide activated by ebselen is presented. We demonstrate that formation of the 2-amino-3H-phenoxazin-3-one core requires that the substituents present on one of the reacting substrate molecules be eliminated under oxidative reaction conditions.

Key words

catalysis - ebselen - heterocycles - peroxides - 2-aminophenols

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References

References
1 New address: Jarosław M. Granda, Institute of Organic Chemistry, Polish Academy of Science, Kasprzaka 44/52, 01-224 Warsaw, Poland.
2 New address: Katarzyna Piekielska-Kulp, Analytische Chemie – Elektroanalytik & Sensorik, Ruhr-Universität Bochum, Universitätsstraße 150, D-44780 Bochum, Germany.

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Supplementary Material

Supporting Information