Analogs of AICA- and ISOAICA ribosides and their methylated base counterparts

Article abstract of DOI:10.1080/07328319908044611

A mild, convenient and efficient synthesis has been developed for imidazole-4-thiocarboxamide and imidazole-5-thiocarboxamide ribosides and the analogous selenocarboxamides. This methodology, i.e., DMF saturated with H₂S or H₂Se, also converts the corresponding N-methylated bases to the corresponding amides. The imidazole-4(5)-selenocarboxamides were shown to be sensitive to base (pH 11) and were easily converted back to their cyano precursors. The kinetics of these reactions were determined and they indicate that the C5 amides were more reactive than their C4 analogs.

Full text of DOI:10.1080/07328319908044611

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Nucleosides and Nucleotides
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Analogs of AICA- and IsoAICA Ribosides
and Their Methylated Base Counterparts
Raymond P. Panzica a & Leroy B. Townsend b
a Departments of Biomedical Sciences and Chemistry , University of
Rhode Island , Kingston, Rhode Island, 02881-0809, USA
b Departments of Medicinal Chemistry and Chemistry , University of
Michigan , Ann Arbor, Michigan, 48109-1065, USA
Published online: 04 Oct 2006.
To cite this article: Raymond P. Panzica & Leroy B. Townsend (1999) Analogs of AICA- and IsoAICA
Ribosides and Their Methylated Base Counterparts, Nucleosides and Nucleotides, 18:11-12, 2345-2356,
DOI: 10.1080/07328319908044611
To link to this article: http://dx.doi.org/10.1080/07328319908044611
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