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Pteridines. Part XLI . Synthesis and properties of 6,7,8‐trimethyl‐4‐thiolumazine
Author(s) -
Hübsch Walter,
Pfleiderer Wolfgang
Publication year - 1989
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.19890720414
Subject(s) - chemistry , amine gas treating , medicinal chemistry , thio , condensation , chloride , sequence (biology) , stereochemistry , organic chemistry , biochemistry , physics , thermodynamics
The first representative of the 8‐substituted 4‐thiolumazine series has been synthesized. In a sequence of reactions, 4,6‐dichloropyrimidin‐2‐(1 H )‐one ( 1 ) is first converted into 4‐chloro‐6‐(methylamino)pyrimidin‐2(1 H )‐one ( 6 ), then the Cl‐atom displaced by the thioxo group (→7) followed by a coupling reaction with 4‐chlorophenyldiazonium chloride to introduce the necessary N‐function into the 5‐position (→ 9 ; Scheme 1 ). Reduction of the p ‐chlorophenylazo group leads to the 6‐(methlyamino)‐4‐thiouracil‐5‐amine ( 10 ) which on condensation with diacetyl gives 6,7,8‐trimethyl‐4‐thiolumazine ( 8 ). The physical properties of 8 are compared with the 2‐thio analog and 6,7,8‐trimethyllumazine indicating that 8 possesses the highest acidity and the longest UV absorption.