Syntheses of 8-aminoimidazo[4',5':5,6]pyrido[2,3-d]pyrimidines: Linear tricyclic analogs of adenine

The syntheses of 8-aminoimidazo[4',5':5,6]pyrido[2,3-d]pyrimidines (7), stretched-out versions of the naturally occuring nucleoside base adenine, are reported. Their preparation involves conversion of purine into 5-aminoimidazo[4,5-b]pyrimidine-6-carbonitrile (1) by reaction with malononit...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 33; no. 2; pp. 319 - 322
Main Authors Harris, PA, Pendergast, W
Format Journal Article
LanguageEnglish
Published TAMPA HETERO CORPORATION 01.03.1996
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIMENSIONAL PROBES
BINDING
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Summary:The syntheses of 8-aminoimidazo[4',5':5,6]pyrido[2,3-d]pyrimidines (7), stretched-out versions of the naturally occuring nucleoside base adenine, are reported. Their preparation involves conversion of purine into 5-aminoimidazo[4,5-b]pyrimidine-6-carbonitrile (1) by reaction with malononitrile, followed by construction of the pyrimidine ring in two steps via the ethoxymethylene derivative 3. 8-Azapurine can be converted to 8-amino-1,2,3-triazolo[4',5':5,6]pyrido[2,3-d]pyrimidines 8 in a similar fashion.
ISSN:0022-152X
DOI:10.1002/jhet.5570330218