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Synthesis of 2‐aminoquinazolines from ortho ‐fluorobenzaldehydes
Author(s) -
Hynes John B.,
Campbell Johnny P.
Publication year - 1997
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.5570340205
Subject(s) - chemistry , substituent , guanidine , carbonate , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry
The reaction of guanidine carbonate with various ortho ‐fluorobenzaldehydes in N,N ‐diinethylacetamide was investigated as a potential route for preparing 2‐aminoquinazolines. Eleven new 2‐aminoquinazolines were elaborated in this manner in low to moderate yields. In general the best results were obtained with ortho ‐fluorobenzaldehydes possessing an electron withdrawing substituent at the other ortho position. Complex mixtures were obtained using 2‐fluorobenzaldehyde, 2,5‐difluorobenzaldehyde and 2‐fluoro‐5‐methoxybenzaldehyde which were not resolved.