Late-Stage Diversification of Imidazole-Based Pharmaceuticals through Pd-Catalyzed Regioselective C-H Bond Arylations

被引：11

作者：

Benzai, Amal ^{[1
,2
]}

Shi, Xinzhe ^{[1
]}

Derridj, Fazia ^{[2
]}

Roisnel, Thierry ^{[1
]}

Doucet, Henri ^{[1
]}

Soule, Jean-Francois ^{[1
]}

机构：

[1] Univ Rennes, CNRS UMR6226, F-3500 Rennes, France

[2] UMMTO Univ, LPCM, BP 17 RP, Tizi Ouzou 15000, Algeria

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 20期

关键词：

2-PHOTON FLUORESCENT-PROBE; DIRECT C-5 ARYLATION; DIRECT C5-ARYLATION; PEPTIDES; ACTIVATION; FUNCTIONALIZATION; COMPLEXES; HETEROARENES; ENABLES; AZOLES;

D O I：

10.1021/acs.joc.9b01469

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed C-H bond arylation of imidazoles has been applied to pharmaceuticals such as Bifonazole, Climbazole, and Prochloraz. In the presence of phosphine-free Pd(OAc)(2) catalyst, aryl bromides are efficiently coupled at the CS-position of the imidazole units, which are widely decorated. Under these conditions, only C-H bond arylation reaction occurred without affecting the integrity of chemical structure of the imidazole-based pharmaceuticals. Moreover, with Bifonazole Pd-catalyzed C-H bond diarylation at the C2- and C5-positions of imidazole unit has also been performed.

引用

页码：13135 / 13143

页数：9

共 40 条

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