Regioselective Synthesis of 2,4-Substituted Pyrido[1,2:1,5]pyrazolo[3,4-d]pyrimidines through Sequential Pd-Catalyzed Arylation and SNAr Reactions

被引：12

作者：

Belaroussi, Rabia ^{[1
,2
]}

El Hakmaoui, Ahmed ^{[2
]}

Akssira, Mohamed ^{[2
]}

Guillaumet, Gerald ^{[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 Mohammedia Casablanca, Lab Chim Phys & Chim Bioorgan, BP 146, Mohammadia 28800, Morocco

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 21期

关键词：

Synthesis design; Cross-coupling; Nucleophilic substitution; Nitrogen heterocycles; Palladium; CROSS-COUPLING REACTIONS; P38 KINASE INHIBITORS; ARYL BORONIC ACIDS; HETEROAROMATIC THIOETHER; TAUTOMERIZABLE HETEROCYCLES; CONVENIENT SYNTHESIS; EFFICIENT ACCESS; PYBROP; DERIVATIVES; PYRIMIDINES;

D O I：

10.1002/ejoc.201600356

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and regioselective functionalization of rare 2,4-disubstituted-pyrido[1,2:1,5]pyrazolo[3,4-d]pyrimidine derivatives is reported. C-4 aminations were performed by chlorine nucleophilic substitution SNAr reactions, and their efficiencies were compared with those for direct one-pot amide C-O activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP) as a reagent. The latter method was used to perform palladium-catalyzed C-4 (het)arylation. Finally, two C-4 amino and aryl derivatives were prepared on a large scale and engaged in desulfurative Liebeskind-Srogl-type reactions under microwave irradiation to afford the envisioned compound library. Each step was optimized, and the results are discussed.

引用

页码：3550 / 3558

页数：9

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