Controlled Dimroth Rearrangement in the Suzuki–Miyaura Cross Coupling of Triazolopyridopyrimidines

Polynitrogen heterocycles are often subject to Dimroth rearrangement which consists of ring opening, bond rotation, and ring closure. In this note, we report a synthesis of two new families of triazolopyridopyrimidines. Successful functionalization via a Suzuki–Miyaura coupling was performed with to...

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Published inJournal of organic chemistry Vol. 81; no. 24; pp. 12506 - 12513
Main Authors Champiré, Anthony, Vala, Christine, Laabid, Achraf, Benharref, Ahmed, Marchivie, Mathieu, Plé, Karen, Routier, Sylvain
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.12.2016
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
isomerization
Material chemistry
new family
organic chemistry
Physical Sciences
Science & Technology
triazoles
CHEMISTRY
INHIBITORS
PYRIDOPYRIMIDINES
RING
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Summary:Polynitrogen heterocycles are often subject to Dimroth rearrangement which consists of ring opening, bond rotation, and ring closure. In this note, we report a synthesis of two new families of triazolopyridopyrimidines. Successful functionalization via a Suzuki–Miyaura coupling was performed with total control of triazole (Dimroth) isomerization based on the judicious choice of reaction conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b02357