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Versatile synthesis of 6‐substituted 8‐deazapteridine‐2,4‐diamines. Formal total synthesis of 8,10‐dideazaminopterin
Author(s) -
Troschütz Reinhard,
Karger Alexander
Publication year - 1996
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.5570330643
Subject(s) - chemistry , aminoketone , guanidine , formal synthesis , stereochemistry , amino acid , total synthesis , organic chemistry , biochemistry
A new synthesis of 4‐amino‐4‐deoxy‐8,10‐dideazapteroic acid ( 11d ) and 6‐substituted and 5,6‐anellated 8‐deazapteridine‐2,4‐diamines, 10a, 10d, 25 , is described. Starting from keteneaminals 1 or 12 and enaminones 4 or β‐aminoketone 17 the title compounds can be prepared via functional group transformation of 2‐amino‐3‐nitropyridines 5 or nicotinate 13a yielding 3‐amino‐α‐picolinonitriles 9 which are cyclocondensed with guanidine.