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A facile synthesis of pyrrolo[3,2-d]pyrimidines from 6-azidouracils and ylide phosphoranes

✍ Scribed by Wafaa M. Abdou; Amin F. M. Fahmy; Azza A. Kamel

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
201 KB
Volume
13
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

A series of the title compounds, 9‐deazaxanthines, was regioselectively prepared in reasonable yields as major products from the reactions of 6‐azidouracils 1a,b with stabilized ester‐2a,b or keto‐2c ylide phosphoranes and a moderated phosphorus ylide 3, instead of the expected triazoles. Side products were also observed wherein pyrimido[5,4‐g]pteridine‐2,4,5,7‐tetrone (15) and other fused ring systems or acyclic‐substituted uracil derivatives were isolated. A comparative study on the reactivity of 1a in analogy to 1b toward phosphoranes is also described. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:357–365, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10048

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