Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C-H Arylation Reactions

被引：67
|
作者：
Cerna, Igor [1 ]
Pohl, Radek [1 ]
Klepetarova, Blanka [1 ]
Hocek, Michal [1 ]
机构：
[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, Global Sci & IOCB Res Ctr, CZ-16610 Prague 6, Czech Republic
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期
关键词：
D O I：
10.1021/jo8018126
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel practical methodology of synthesis of a several types of di-, tri-, and tetraarylpurine derivatives by a combination of regioselective Suzuki cross-coupling reactions and/or Cu-catalyzed N-arylation with direct C-H arylations was developed. 6,8-Diaryl- and 2,6,8-triaryl-9-isopropylpurines were prepared by one or two cross-couplings of 6-chloro- or 2,6-dichloro-9-isopropylpurine with arylboronic acids followed by Pd-catalyzed C-H arylation by aryl halides to position 8. 6-Chloropurine and adenine underwent Cu-catalyzed N-arylation to position 9 with boronic acids, followed by cross-coupling with AlMe3 and/ or C-H arylation to obtain 8,9-diaryl-6-methylpurines or 8,9-diaryladenines (accompanied by products of partial N-arylation of adenine in position 6). The methodology is suitable for construction of small libraries of modified purines.
引用
收藏
页码：9048 / 9054
页数：7
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