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

A complete study on the preparation of original halogen‐containing 4 H ‐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 ser...

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Published in:European journal of organic chemistry 2015-06, Vol.2015 (17), p.3830-3840
Main Authors: Le Falher, Laetitia, Ben Ayad, Omar, Ziyaret, Ozge, Botuha, Candice, Thorimbert, Serge, Slowinski, Franck
Format: Article
Language:English
Subjects:
Chemical Sciences
Life Sciences
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Summary:A complete study on the preparation of original halogen‐containing 4 H ‐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 4 H ‐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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500277