Synthesis of Multisubstituted 1,4-Dihydrobenzoxazin-2-ones through a One-Pot Nucleophilic N-Alkylation/C-Alkylation of Cyclic α-Imino Esters

Lode De Munck; Carlos Vila; Carolina Pons; José R. Pedro

doi:10.1055/s-0036-1588742

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(12): 2683-2690
DOI: 10.1055/s-0036-1588742

paper

Synthesis of Multisubstituted 1,4-Dihydrobenzoxazin-2-ones through a One-Pot Nucleophilic N-Alkylation/C-Alkylation of Cyclic α-Imino Esters

Authors

Lode De Munck

Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain eMail: carlos.vila@uv.es eMail: jose.r.pedro@uv.es
Carlos Vila*

Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain eMail: carlos.vila@uv.es eMail: jose.r.pedro@uv.es
Carolina Pons

Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain eMail: carlos.vila@uv.es eMail: jose.r.pedro@uv.es
José R. Pedro*

Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain eMail: carlos.vila@uv.es eMail: jose.r.pedro@uv.es

Abstract

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Abstract

A nucleophilic N-alkylation of 2-oxobenzoxazine-2-carboxylates with organozinc reagents with good selectivities and in moderate to good yields is described. Moreover, the synthesis of multisubstituted 1,4-dihydrobenzoxazine-2-ones bearing a tetrasubstituted carbon atom via a one-pot N-alkylation/C-alkylation reactions is reported.

Key words

dihydrobenzoxazinone - umpolung - zinc - tetrasubstituted carbon - one-pot reaction - cyclic α-imino esters

Volltext

Referenzen

References

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