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Chemoselective Access to π‐Conjugated Heterocycles by Stille and Sonogashira Reactions on 2‐Substituted 4 H ‐Pyrido[ e ][1,3]oxazin‐4‐ones
Author(s) -
Le Falher Laetitia,
Mumtaz Amara,
Nina Diogo Anthony,
Thorimbert Serge,
Botuha Candice
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601338
Subject(s) - sonogashira coupling , stille reaction , chemistry , conjugated system , aryl , combinatorial chemistry , coupling reaction , stereochemistry , palladium , organic chemistry , catalysis , polymer , alkyl
Site‐selective Pd II ‐catalyzed cross‐coupling reactions of 2‐substituted‐4 H ‐pyrido[ e ][1,3]oxazin‐4‐ones were developed. C4‐ and C5‐alkynylated pyridooxazinones were thus obtained through Sonogashira coupling, whereas the efficient incorporation of (hetero)aryl and ethenyl substituents at the C5 position was achieved by Stille coupling. Finally, an example of one‐pot sequential multiple Sonogashira reactions with different alkynes was realized. The strategy developed herein provides rapid access to polyfunctionalized precursors with extended π‐conjugation for further application as fluorescent materials.