title: Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines.
abstract: A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
authors.forename: Jian-Ping
authors.initials: JP
authors.lastname: Lin
authors.forename: Feng-Hua
authors.initials: FH
authors.lastname: Zhang
authors.forename: Ya-Qiu
authors.initials: YQ
authors.lastname: Long
mesh_terms: D000578:Amidines / Q000737:chemistry*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008670:Metals; D015394:Molecular Structure; D016877:Oxidants; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D000578:Amidines; D001562:Benzimidazoles; D008670:Metals; D016877:Oxidants; D011799:Quinazolines; D012997:Solvents