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A New Synthesis of Pteridines
Author(s) -
Xu Ming,
Vasella Andrea
Publication year - 2006
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.200690111
Subject(s) - chemistry , intramolecular force , isomerization , pteridine , stereochemistry , cycloaddition , acylation , cleavage (geology) , side chain , medicinal chemistry , organic chemistry , polymer , geotechnical engineering , fracture (geology) , engineering , enzyme , catalysis
A new synthesis of pteridines possessing a (substituted) ( Z )‐3‐hydroxyprop‐1‐enyl group at C(6) is based on the acylation of 4‐amino‐5‐nitrosopyrimidines with dienoic acid chlorides, followed by a high‐yielding intramolecular hetero‐ Diels–Alder cycloaddition and cleavage of the NO bond leading to 4 . Thermolysis of the resulting pteridines 4 possessing a benzyloxy group at C(4) led to the products 5 , resulting from isomerisation of the 3‐hydroxyprop‐1‐enyl to an 3‐oxopropyl side chain, while the analogous pteridine 8 possessing an NH 2 group at C(4) remained unaffected.