TBHP as Methyl Source under Metal‐Free Aerobic Conditions To Synthesize Quinazolin‐4(3H)‐ones and Quinazolines by Oxidative Amination of C(sp³)–H Bond

Abstract

tert‐Butyl hydroperoxide (TBHP) served as the methyl source under metal‐free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin‐4(3H)‐ones and quinazolines from 2‐aminobenzamides and 2‐carbonyl‐substituted anilines, respectively.

Thermo-Promoted Reactions of Anthranils with Carboxylic Acids, Amines, Phenols, and Malononitrile under Catalyst-Free Conditions

“…HRMS (ESI) m / z [M + H] + calcd for C 13 H 12 BrN 2 O 291.0133, found 291.0128. The characterization data is consistent with reported literature …”

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.86 (s, 1H), 7.79 (br, 1H), 7.45 (t, J = 6.4 Hz, 2H), 7.27 (d, J = 8.0 Hz, 2H), 7.24−7.20 (m, 1H), 6.71 (t, J = 7.6 Hz, 2H), 5.50 (br, 2H). 13 27 2-Amino-N-(3,5-dimethylphenyl)benzamide (5e). White solid (187 mg, 78%).…”

“…The characterization data is consistent with reported literature. 27 2-Amino-4-methoxy-N-phenylbenzamide (5j). White solid (198 mg, 82%).…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.28 (d, J = 8.0 Hz, 1H), 7.19 (t, J = 7.6 Hz, 1H), 6.65 (dd, J = 7.6, 14.8 Hz, 2H), 5.89 (br, 1H), 5.47 (br, 2H), 3.92 (td, J = 7.2, 14.4 Hz, 1H), 2.01 (d, J = 9.6 Hz, 2H), 1.75 (dd, J = 3.6, 10.0 Hz, 2H), 1.65 (d, J = 12.8 Hz, 1H), 1.42 (dd, J = 12.4, 24.8 Hz, 2H), 1.23 (dt, J = 8.8, 18.0 Hz, 3H). 13 27 2-(Benzo [d]thiazol-2-yl)aniline (5m). Yellow solid (169 mg, 75%).…”

Phenazine Derivatives with Anti-Inflammatory Activity from the Deep-Sea Sediment-Derived Yeast-Like Fungus Cystobasidium laryngis IV17-028

“…To a solution of 2-aminobenzoic acid (50.0 mg, 0.36 mM) in toluene (1.2 mL) was added thionyl chloride solution (1.8 mL, 1.8 mM) at room temperature and the mixture was refluxed for 3 h. After completion of the reaction was confirmed by TLC, the solvent was removed under vacuum to obtain the crude acid chloride as yellow oil, which was used for further reaction without purification [12].…”