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Microwave‐Assisted [3+2] Cycloaddition and Suzuki–Miyaura Cross‐Coupling for a Concise Access to Polyaromatic Scaffolds
Author(s) -
Hédou Damien,
Deau Emmanuel,
DubouilhBenard Carole,
Sanselme Morgane,
Martinet Anthony,
Chosson Elizabeth,
Levacher Vincent,
Besson Thierry
Publication year - 2013
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.201301014
Subject(s) - chemistry , cycloaddition , combinatorial chemistry , halogenation , one pot synthesis , organic chemistry , catalysis
Novel 3‐(prop‐2‐ynyl)pyrido[2,3‐ d ]pyrimidin‐4(3 H )‐ones and 3‐(prop‐2‐ynyl)quinazolin‐4(3 H )‐ones have been synthesized in a high‐yielding microwave‐assisted one‐pot procedure. The one‐pot sequence was conveniently extended to the synthesis of commercially unavailable 6‐bromo‐ N 3 ‐propargylpyrido[2,3‐ d ]pyrimidinone by a regiocontrolled bromination with NBS. The synthetic scaffolds were successfully converted into triazoles by copper(I)‐catalyzed [3+2] cycloaddition and substituted at the 6‐position by Suzuki–Miyaura cross‐coupling in high overall yields.