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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