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

被引：7
作者：
Ejjoummany, Abdelaziz [1 ,2 ]
Belaroussi, Rabia [1 ,2 ]
El Hakmaoui, Ahmed [2 ]
Akssira, Mohamed [2 ]
Guillaumet, Gerald [1 ]
Buron, Frederic [1 ]
Routier, Sylvain [1 ]
机构：
[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, UMR 7311, BP 6759, F-45067 Orleans 2, France
[2] Univ Hassan II Casablanca, Lab Chim Phys & Chim Bioorgan, BP 146, Mohammadia 28800, Morocco
来源：
MOLECULES | 2018年 / 23卷 / 11期
关键词：
pyridopyrazolopyrimidine; pyBroP activation; palladium cross-coupling; DISCOVERY; RING; HETEROCYCLES; SYSTEMS; DESIGN; ACCESS; SERIES; SNAR;
D O I：
10.3390/molecules23112740
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
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页数：15
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