Synthesis of the pyrido[4,3-d]pyrimidine congeners of inosine and of adenosine - A new class of 6:6 bicyclic C-ribofuranosides Journal Article


Authors: Rao, K. V. B.; Klein, R. S.; Sarma, M. S. P.; Otter, B. A.
Article Title: Synthesis of the pyrido[4,3-d]pyrimidine congeners of inosine and of adenosine - A new class of 6:6 bicyclic C-ribofuranosides
Abstract: The synthesis of the pyrido[4,3-d]pyrimidine congeners (7 and 8) of inosine and adenosine from the known precursor 3-dimethylamino-2-(2,3-O-isopropylidene-5-O-trityl-D-ribofuranosyl)acrylonitrile (10) is described. The synthetic sequence involves a modified Thorpe-Ziegler annulation to a 4-amino-3-cyanotetrahydropyridine derivative (22) followed by aromatization to an alpha, beta mixture of the desired 5-ribosyl-4-amino-3-cyanopyridine intermediates (25 and 26). Further annulation to the pyrido[4,3-d]pyrimidine ring system and simultaneous detritylation and deisopropylidenation completes the synthesis.
Keywords: precursor; cells; analogs; culture; agent; configuration; pneumocystis-carinii; leishmania-donovani; nucleoside isostere; 9-deazaadenosine
Journal Title: Nucleosides & Nucleotides
Volume: 11
Issue: 1
ISSN: 0732-8311
Publisher: Taylor & Francis Inc.  
Date Published: 1992-01-01
Start Page: 61
End Page: 83
Language: English
ACCESSION: WOS:A1992HA67900006
DOI: 10.1080/07328319208021153
PROVIDER: wos
Notes: Article -- Source: Wos
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