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Paper | Regular issue | Vol 55, No. 10, 2001, pp.1873-1888
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9302
Regioselective Formylation of Ethyl 3,4-Dihydro-2H-1,4- benzoxazine-2-carboxylate or 2-Acetate Derivatives

Stanislas Mayer, Gérald Guillaumet, and Jean-Yves Mérour*

*Institut de Chimie Organique et Analytique, UMR CNRS 6005, BP 6759, Université d'Orléans, Rue de Chartres, 45067 Orléans Cédex 2, France

Abstract

Formylation reactions on ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate or 2-acetate derivatives were carried out using either Vilsmeier-Haack’s conditions or Rieche’s method. 7-Formyl compounds were exclusively obtained from N-benzyl-3,4-dihydro-2H-1,4-benzoxazines derivatives through Vilsmeier’s procedure. A mixture of 6- and 8-formyl compounds, where the isomer in position-6 was predominant, was formed using the Rieche’s method.