SYNTHESIS OF 2-AMINOQUINAZOLINES FROM ORTHO-FLUOROBENZALDEHYDES

The reaction of guanidine carbonate with various ortho-fluorobenzaldeh ydes in N,N-dimethylacetamide was investigated as a potential route fo r preparing 2-aminoquinazolines, Eleven new 2-aminoquinazolines were e laborated in this manner in low to moderate yields. In general the bes t results were obtained with ortho-fluorobenzaldehydes possessing an e lectron withdrawing substituent at the other ortho position. Complex m ixtures were obtained using 2-fluorobenzaldehyde, 2,5-difluorobenzalde hyde and 2-fluoro-5-methoxybenzaldehyde which were not resolved.