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Unequivocal syntheses of 6‐methyl‐ and 6‐phenylisoxanthopterin
Author(s) -
Neilsen J. Bryant,
Broadbent H. Smith,
Hennen William J.
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240624
Subject(s) - chemistry , alkoxy group , amino acid , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , alkyl
Although 6‐methyl‐ ( 1 ) and 6‐phenylisoxanthopterin ( 2 ) have previously been synthesized, the requirement of high purity necessary for immunological testing has necessitated our development of the first reported synthesis of these compounds by unequivocal methods. In the process of so doing four new pyrazines, ethyl 3‐amino‐5‐chloro‐6‐methyl‐2‐pyrazinecarboxylate ( 11 ), N,N ‐dimethyl‐ N '‐(6‐chloro‐3‐cyano‐5‐phenylpyrazin‐2‐yl)methanimidamide ( 16 ), 2‐amino‐3‐ethoxycarbonyl‐5‐phenylpyrazine 1‐oxide ( 19 ), and ethyl 3‐amino‐5‐chloro‐6‐phenyl‐2‐pyrazinecarboxylate ( 20 ) were synthesized. Four new pteridines, 7‐methoxy‐6‐methyl‐2,4‐pteridinediamine ( 7 ), 7‐methoxy‐6‐phenyl‐2,4‐pteridinediamine ( 17 ), 2‐amino‐7‐ethoxy‐6‐methyl‐4(3 H )‐pteridinone ( 12 ), and 2‐amino‐7‐ethoxy‐6‐phenyl‐4(3 H )‐pteridinone ( 21 ) have also been synthesized enroute to these isoxanthopterins.