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DOI: 10.1055/s-0029-1216640
Synthesis of Fluorinated Pyrrolo[2,3-b]pyridine and Pyrrolo[2,3-d]pyrimidine Nucleosides
Publication History
Publication Date:
12 May 2009 (online)
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Abstract
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.
Key words
pyrrole - amine - fluorine - pyridine - annulation - electrophilic aromatic substitution
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References
Crystallographic data (excluding structure
factors) for the structures reported in this paper have been deposited
with the Cambridge Crystallographic Data Centre as supplementary publication
no. CCDC 703680 and CCDC 683574 can be obtained free of charge on
application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033;
e-mail:
deposit@ccdc.cam.ac.uk.