Selective, Catalytic, and Dual C(sp³)-H Oxidation of Piperazines and Morpholines under Transition-Metal-Free Conditions

Delfino Chamorro-Arenas, Urbano Osorio-Nieto, Leticia Quintero, Luís Hernández-García, Fernando Sartillo-Piscil*

*Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 14 Sur Esq. San Claudio, Col. San Manuel, Puebla 72570, México, Email: fernando.sartillocorreo.buap.mx

D. Chamorro-Arenas, U. Osorio-Nieto, L. Quintero, L. Hernández-García, F. Sartillo-Piscil, J. Org. Chem., 2018, 83, 15333-15346.

DOI: 10.1021/acs.joc.8b02564

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Abstract

The use of cheap and innocuous reagents, such as NaClO₂, NaOCl, and catalytic amounts of TEMPO enables an environmentally friendly C(sp³)-H oxidation of piperazines and morpholines to 2,3-diketopiperazines and 3-morpholinones, respectively. In addition, by using a stoichiometric amount of TEMPO, 2-alkoxyamino-3-morpholinones can be prepared from morpholine derivatives.

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Key Words

N-heterocycles, NaClO₂, NaOCl, TEMPO

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ID: J42-Y2018