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Synthesis and Reactivity in [3+2] Cycloadditions of Isoxanthopterin N(5) ‐Oxides – A New Synthesis of 6‐Substituted Pteridinediones
Author(s) -
Steinlin Thomas,
Sonati Tiziana,
Vasella Andrea
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890201
Subject(s) - chemistry , intramolecular force , cycloaddition , stereochemistry , reactivity (psychology) , cleavage (geology) , pteridine , 1,3 dipolar cycloaddition , oxide , side chain , nitrone , medicinal chemistry , purine , bicyclic molecule , organic chemistry , enzyme , medicine , polymer , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering , catalysis
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).