Chemoselective Access to π-Conjugated Heterocycles by Stille and Sonogashira Reactions on 2-Substituted 4H-pyrido[e][1,3]oxazin-4-ones - Sorbonne Université Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2017

Chemoselective Access to π-Conjugated Heterocycles by Stille and Sonogashira Reactions on 2-Substituted 4H-pyrido[e][1,3]oxazin-4-ones

Abstract

Site-selective Pd(II) catalyzed cross-coupling reactions have been developed on 2-substituted-4H-pyrido[e][1,3]oxazin-4-ones. C 4-and C 5-alkynylated pyridooxazinones have been thus obtained via Sonogashira reaction while the efficient incorporation at C 5 position of (hetero)aryl, ethenyl substituents have been achieved via Stille reaction. Finally one example of a one pot sequential multiple Sonogashira reaction with different alkynes has been realized. The strategy developed herein provides a rapid access to polyfunctionnalized precursors with extended π-conjugation for further application as fluorescent material.
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Dates and versions

hal-01520273 , version 1 (10-05-2017)

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Laetitia Le Falher, Amara Mumtaz, Anthony Nina Diogo, Candice Botuha, Serge Thorimbert. Chemoselective Access to π-Conjugated Heterocycles by Stille and Sonogashira Reactions on 2-Substituted 4H-pyrido[e][1,3]oxazin-4-ones. European Journal of Organic Chemistry, 2017, 2017 (4), pp.827-832. ⟨10.1002/ejoc.201601338⟩. ⟨hal-01520273⟩
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