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Benzo4,5imidazo1,2-cquinazoline-6-carbonitriles are prepared in high yields via three new routes: (1) a Cu(OTf)2 (0-5 mol %) catalyzed hypervalent iodine PhI(OTf)2 mediated oxidative coupling of 4-anilinoquinazoline-2-carbonitriles in neat trifluoroacetic acid (TFA); (2) a Pd(OAc)2 (10 mol %) or CuI (10 mol %) mediated nonoxidative coupling of 4-(2-bromoanilino)quinazoline-2-carbonitrile; and (3) a nonoxidative Pd(Ar3P)3 Ar = 3,5-(F3C)2C6H3 aka Superstable Pd(0) Catalyst (10 mol %) mediated intramolecular C-N cyclization of 3-(2-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitriles. All new compounds are fully characterized.
Proser et al. (Sat,) studied this question.