Preparation of Halogen-Containing 4 H -Pyrido[e][1,3]oxazin-4-ones and Their Transformation into 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles and 1,2,4-Triazoles - Institut Parisien de Chimie Moléculaire Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2015

Preparation of Halogen-Containing 4 H -Pyrido[e][1,3]oxazin-4-ones and Their Transformation into 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles and 1,2,4-Triazoles

Omar Ben Ayad
  • Fonction : Auteur
Ozge Ziyaret
  • Fonction : Auteur
Candice Botuha
Serge Thorimbert

Résumé

A complete study on the preparation of original halogen-containing 4H-pyrido[e][1,3]oxazin-4-ones and their transformation into 1,2,4-oxadiazoles and 1,2,4-triazoles is presented. Starting from pyridyl-imide sodium salts, the efficiency of the intramolecular O-arylation was studied on three series of compounds, with different fluoro-, chloro-, and bromophenyl substituents at the C-2 position. The final halogenated compounds are of interest as new synthons for future functionalisation. We also present the discovery of a new, rapid, and complementary access to 2-substituted 4H-benzo[e][1,3]oxazinones. Finally, the one-step transformation of some of these pyrido-oxazinones into the corresponding hydroxypyridyl-substituted 1,2,4-oxadiazoles and 1,2,4-triazoles was explored, and the regioselectivity of the reaction was proved by X-ray crystallography.

Dates et versions

hal-01624683 , version 1 (26-10-2017)

Identifiants

Citer

Laetitia Le Falher, Omar Ben Ayad, Ozge Ziyaret, Candice Botuha, Serge Thorimbert, et al.. Preparation of Halogen-Containing 4 H -Pyrido[e][1,3]oxazin-4-ones and Their Transformation into 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles and 1,2,4-Triazoles. European Journal of Organic Chemistry, 2015, 2015 (17), pp.3830--3840. ⟨10.1002/ejoc.201500277⟩. ⟨hal-01624683⟩
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