Specific inhibitors in vitamin biosynthesis. Part 10. Synthesis of 7- and 8-substituted 7-deazaguanines

Autor:	Kyuji Ohta, Colin L. Gibson, K. Paulini, Colin J. Suckling
Rok vydání:	1998
Předmět:	Annulation Stereochemistry Chemistry Electrophile Substrate (chemistry) Vitamin biosynthesis
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :3025-3032
ISSN:	1364-5463 0300-922X
Popis:	Versatile syntheses of 7- and 8-substituted 7-deazaguanines including N-alkyl derivatives have been developed by identifying selective annulation reactions with 2,6-diaminopyrimidin-4(3H)-one as substrate and β-halocarbonyl compounds as electrophiles. A new synthesis of 8-substituted 7-deazaguanines using nitrosoalkenes as electrophiles is described. With some combinations of reactants, furo[2,3-d]pyrimidines are significant products in place of or in addition to the required 7-deazaguanines [pyrrolo[2,3-d]-pyrimidin-4(3H)-ones]. When 2,4-diamino-6-chloropyrimidine was used as a substrate, imidazopyrimidines were produced.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9f6dda226d9e9155b38e55201393749b https://doi.org/10.1039/a804037k Zobrazit plný text záznamu