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Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1',2':1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions.


ABSTRACT: The design of some novel di-(het)arylated-3H-pyrido[1',2':1,5]pyrazolo[4,3-d]pyrimidine derivatives is reported. The series was developed from 1-aminopyridinium iodide, which afforded the key intermediate bearing two thiomethyl and amide functions, each of them useful for palladium catalyzed cross coupling reactions by alkyl sulfur release and C-O activation, respectively. The two regioselective and successive cross-coupling reactions were first carried out in C-4 by in situ C-O activation and next in C-2 by a methylsulfur release. Process optimization furnished conditions leading to products in high yields. The scope and limitations of the methodologies were evaluated and the final compounds characterized.

SUBMITTER: Ejjoummany A 

PROVIDER: S-EPMC6278517 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1',2':1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions.

Ejjoummany Abdelaziz A   Belaroussi Rabia R   El Hakmaoui Ahmed A   Akssira Mohamed M   Guillaumet Gérald G   Buron Frédéric F   Routier Sylvain S  

Molecules (Basel, Switzerland) 20181023 11


The design of some novel di-(het)arylated-3<i>H</i>-pyrido[1',2':1,5]pyrazolo[4,3-<i>d</i>]pyrimidine derivatives is reported. The series was developed from 1-aminopyridinium iodide, which afforded the key intermediate bearing two thiomethyl and amide functions, each of them useful for palladium catalyzed cross coupling reactions by alkyl sulfur release and C-O activation, respectively. The two regioselective and successive cross-coupling reactions were first carried out in C-4 by in situ C-O ac  ...[more]

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