si-quinazolinone.docVIP

Supporting Information for CuBr2-Catalyzed Ullmann-type Coupling and Benzylic C-H Amidation: A Strategy to Construct 2-Aryl Quinazolinones by Domino Reactions Lixia Wang, Junfeng Xiang, Yalin Tang* Beijing National Laboratory for Molecular Sciences (BNLMS), Center for Molecular Sciences, State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China E-mail: tangyl@iccas.ac.cn. Table of contents General informantion S2 Synthesis of quinazolinone derivatives 3a-h S2 Synthesis of Ullmann-type products 4a, 4i-j S6 References S7 Copies of 1H and 13C NMR Spectra S8 1. General information All reactions were carried out under Ar atmosphere. Chemical shifts are reported in ppm versus tetramethylsilane with either tetramethylsilane or the residual solvent resonance used as an internal standard. Melting points are uncorrected. 2. General procedure for synthesis of quinazolinone derivatives (3a-h): under argon protection (1 atm, with extrusion of air), a mixture of 2-iodobenzamide (1a, 0.5 mmol, 124 mg), arylmethanamine or α-substituted benzylamine (2, 1.0 mmol), K2CO3 (1.5 mmol, 207 mg) and CuBr2 (0.05 mmol, 11 mg) in DMSO (5 mL) was allowed to stir at 130 oC for several hours (see Table 2 in text). After completion of the reaction, the resulting solution was cooled to room temperature and filtered, and the solvent of filtrate was removed with the aid of a rotary evaporator. The residue was purified by column chromatography on silica gel using petroleum ether/ ethyl acetate as eluent to provide the desired product (3). 2-Phenylquinazolin-4(3H)-one (3a).1 Eluent: petroleum ether/ethyl acetate (3:1). Yield 91 mg (82%). White sol