TY - JOUR
T1 - The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings
AU - Mirallai, Styliana I.
AU - Koutentis, Panayiotis A.
PY - 2015/8/21
Y1 - 2015/8/21
N2 - Benzo[4,5]imidazo[1,2-c]quinazoline-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.
AB - Benzo[4,5]imidazo[1,2-c]quinazoline-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.
UR - http://www.scopus.com/inward/record.url?scp=84940062555&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b01514
DO - 10.1021/acs.joc.5b01514
M3 - Article
AN - SCOPUS:84940062555
SN - 0022-3263
VL - 80
SP - 8329
EP - 8340
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -