title: Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines.
abstract: A traceless polymer-supported synthesis of 4-benzoylquinazolines was developed using the following commercially available building blocks: Fmoc-α-amino acids, 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The acyclic intermediates underwent base-catalyzed rearrangement involving C-C and N-N bond formation followed by ring expansion and yielded resin-bound dihydroquinazoline-2-carboxylic acids. After they were released from the resin by treatment with trifluoroacetic acid, base-mediated decarboxylation produced the target quinazolines in moderate-to-high yields and purities.
authors.affiliation: †Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacky University, 17. listopadu 12, 771 46 Olomouc, Czech Republic.
authors.forename: Veronika
authors.initials: V
authors.lastname: Fülöpová
authors.affiliation: ‡Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States.
authors.forename: Lauren
authors.initials: L
authors.lastname: Cziesla
authors.affiliation: ‡Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States.
authors.forename: Megan
authors.initials: M
authors.lastname: Fleming
authors.affiliation: ‡Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States.
authors.forename: Yiwei
authors.initials: Y
authors.lastname: Lu
authors.affiliation: ‡Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States.
authors.forename: Adrienne
authors.initials: A
authors.lastname: Voelker
authors.affiliation: †Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacky University, 17. listopadu 12, 771 46 Olomouc, Czech Republic.|‡Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States.
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchňák
mesh_terms: D000098:Acetophenones / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000098:Acetophenones; D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D009578:Nitrobenzenes; D011799:Quinazolines; C013190:phenacyl bromide; C002732:2-nitrobenzenesulfenyl chloride
keywords: amino acids; bromoketone; indazole oxides; nitrobenzenesulfonyl chlorides; quinazolines; solid-phase synthesis; traceless synthesis; α-bromoacetophenones