Synthesis of Fluorinated Pyrrolo[2,3-b]pyridine and Pyrrolo[2,3-d]pyrimidine Nucleosides

被引：38

作者：

Iaroshenko, Viktor O. ^{[1
,2
]}

Wang, Yan ^{[3
]}

Sevenard, Dmitri V. ^{[4
]}

Volochnyuk, Dmitriy M. ^{[1
,5
]}

机构：

[1] Enamine Ltd, UA-01103 Kiev, Ukraine

[2] Natl Taras Shevchenko Univ, UA-01033 Kiev 33, Ukraine

[3] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

[4] Hansa Fine Chem GmbH, BITZ, D-28359 Bremen, Germany

[5] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev 94, Ukraine

来源：

SYNTHESIS-STUTTGART | 2009年 / 11期

关键词：

pyrrole; amine; fluorine; pyridine; annulation; electrophilic aromatic substitution; EDITING ADENOSINE-DEAMINASE; DIELS-ALDER REACTIONS; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; ANALOGS; INHIBITION; PHOSPHATE; DESIGN; PURINES; CANCER;

D O I：

10.1055/s-0029-1216640

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With the Purpose of synthesizing novel ADAs (adenosine deaminase) and IMPDH (inosine 5'-monophosphate dehydrogenase) inhibitors the reactions of 5-amino-1-tert-butyl-1-H-pyrrole-3-carbonitrile with fluorinated 1,3-bielectrophiles were studied. An efficient and convenient synthetical approach to fluorinated pyrrolo[2,3-b]pyridines was developed. The tert-butyl protecting group was successfully removed by treating the pyrrolopyridines or -pyrimidines with 60% Sulfuric acid and this was followed by direct glycosylation of the products.

引用

页码：1851 / 1857

页数：7

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