Synthesis of Quinazoline C-Nucleosides: A New Class of 6:6 Bicyclic Purine-Like Analogues.1 |
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| Authors: | Mallela S. P. Sarma Phyllis Wilson Brian A. Otter Robert S. Klein |
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| Affiliation: | Albert Einstein College of Medicine Cancer Center and Medicinal Chemistry Laboratory, Department of Oncology, Montefiore Medical Center , Bronx, NY, 10467-2401 |
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| Abstract: | Abstract The quinazoline C-nucleoside congeners of adenosine (1) and inosine (2) have been obtained by radical-induced addition of 4-bromobutyronitrile to C-ribosyl acrylonitrile 10. A base-catalyzed Ziegler-Thorpe cyclization of the dinitrile thus obtained (11) followed by aromatization with DDQ afforded key intermediate 6-ribosylated anthranilonitrile 14 and its α-isomer. Annulation of a pyrimidine ring onto 14 or onto the corresponding o-amino-amide followed by deblocking with MeOH/HCl finally gave 1 or 2 respectively. |
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