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

Styliana I. Mirallai, Panayiotis A. Koutentis

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8329-8340
Number of pages12
JournalJournal of Organic Chemistry
Volume80
Issue number16
DOIs
Publication statusPublished - 21 Aug 2015

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