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Molecules 2018, 23(11), 2740; https://doi.org/10.3390/molecules23112740

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

1
Institut de Chimie Organique et Analytique, Univ Orleans, UMR CNRS 7311, BP 6759, F-45067 Orléans CEDEX 2, France
2
Laboratoire de Chimie Physique et Chimie Bioorganique, Université Hassan II-Casablanca, B. P. 146, 28800 Mohammedia, Morocco
*
Authors to whom correspondence should be addressed.
Received: 28 September 2018 / Revised: 15 October 2018 / Accepted: 20 October 2018 / Published: 23 October 2018
(This article belongs to the Collection Heterocyclic Compounds)
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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. View Full-Text
Keywords: pyridopyrazolopyrimidine; pyBroP activation; palladium cross-coupling pyridopyrazolopyrimidine; pyBroP activation; palladium cross-coupling
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ejjoummany, A.; Belaroussi, R.; El Hakmaoui, A.; Akssira, M.; Guillaumet, G.; Buron, F.; Routier, S. 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. Molecules 2018, 23, 2740.

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