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Concise and Efficient Access to 5,7‐Disubstituted Pyrazolo[1,5‐ a ]pyrimidines by Pd‐Catalyzed Sequential Arylation, Alkynylation and SN Ar Reaction
Author(s) -
Jismy Badr,
Guillaumet Gérald,
Allouchi Hassan,
Akssira Mohamed,
Abarbri Mohamed
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.201701024
Subject(s) - hexafluorophosphate , reagent , chemistry , catalysis , alkynylation , combinatorial chemistry , activator (genetics) , medicinal chemistry , organic chemistry , ionic liquid , biochemistry , gene
A simple and efficient method for synthesis of 5,7‐disubstituted pyrazolo[1,5‐ a ]pyrimidines is reported. The synthetic route involved first a one‐pot two‐step synthesis of 7‐substituted pyrazolo[1,5‐ a ]pyrimidin‐5‐ones from the reaction of 3‐aminopyrazole 1 with activated alkynes. These compounds were used as key intermediates to access, with excellent yields, a library of new 5,7‐disubstituted pyrazolo[1,5‐ a ]pyrimidines, which are known for their wide range of biological activities, through C–O bond activation with PyBroP (bromotripyrrolidinophosphonium hexafluorophosphate) as an activator reagent.