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Further studies on the synthesis of quinazolines from 2‐fluorobenzonitriles
Author(s) -
Hynes John B.,
Tomažič Alenka,
Parrish Christie A.,
Fetzer Oliver S.
Publication year - 1991
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.5570280530
Subject(s) - chemistry , guanidine , yield (engineering) , reagent , carbonate , organic chemistry , potassium carbonate , combinatorial chemistry , metallurgy , materials science
Recently, we reported that appropriately substituted 2‐fluorobenzonitriles undergo cyclization with guanidine carbonate to afford 2,4‐diaminoquinazolines usually in good to excellent yield. This paper describes the preparation of a variety of new 2,4‐diaminoquinazolines substituted at positions five or seven. In addition, the reactions of selected 2‐fluorobenzonitriles with formamidine acetate or acetamidine acetate were examined. The results obtained demonstrate that the analogous 4‐amino‐ and 2‐methyl‐4‐aminoquinazolines can be prepared by this approach but that the yields are considerably lower than when guanidine carbonate is employed as the cyclization reagent.