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Direct synthesis of 2,4‐diaminoquinazolines from 2‐fluorobenzonitriles
Author(s) -
Hynes John B.,
Pathak Alpana,
Panes Constantina H.,
Okeke Claudia C.
Publication year - 1988
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.5570250425
Subject(s) - chemistry , yield (engineering) , guanidine , ring (chemistry) , generality , primary (astronomy) , group (periodic table) , stereochemistry , transformation (genetics) , medicinal chemistry , combinatorial chemistry , organic chemistry , psychology , biochemistry , materials science , physics , astronomy , metallurgy , psychotherapist , gene
In a search for new methods for preparing 2,4‐diaminoquinazolines having a diversity of substituents in the benzenoid ring, it was found that the reaction of 2,6‐difluorobenzonitrile with guanidine carbonate gave 2,4‐diamino‐5‐fluoroquinazoline in excellent yield. Extension of this approach to other 2‐fluorobenzonitriles, some of which were elaborated for the first time, showed that this reaction possesses considerable generality. The cyclization was successful even when electron donating groups were present at position six. Only in two cases where a primary or secondary amino group was also present ortho to the cyano group was this transformation unsuccessful.