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Synthesis and Reactivity in [3+2] Cycloadditions of Isoxanthopterin N(5)-Oxides – A New Synthesis of 6-Substituted Pteridinediones

✍ Scribed by Thomas Steinlin; Tiziana Sonati; Andrea Vasella

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
218 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Intramolecular condensation of the N‐(4‐amino‐5‐nitrosopyrimidin‐4‐yl)‐2‐chloroacetamide 2 led to the pteridinone N(5)‐oxide 4, while treatment of 2 with Me~3~P yielded the 8‐(chloromethyl)purine 3. A high‐yielding [3+2] dipolar cycloaddition of the N(5)‐oxide 4 to electron‐poor dipolarophiles, followed by spontaneous N,O‐bond cleavage, gave the C(6)‐substituted pteridinones 8a–8d that were deprotected to provide the pteridine‐4,7(3__H__,8__H__)‐diones 9a–9d, constituting a new synthesis of pterinones possessing a functionalised side chain at C(6).

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