Ammonium Chloride–Catalyzed One-Pot Synthesis of 4(3H)-Quinazolinones Under Solvent-Free Conditions

Abstract

ContentsI. Syhthesis and NMR spectral data of 2-amino-3-bromobenzoic acid methyl ester 2 II. NMR spectrum of 2-amino-3-bromobenzoic acid methyl ester 3 III. Typical procedure for the NH 4 Cl-catalyzed synthesis of 4(3H)-quinazolinones under solvent-free conditions 4 IV. NMR spectral data of 4(3H)-quinazolinones 4 V. NMR spectrum of 4(3H)-quinazolinones 7

Access to Phosphine-Containing Quinazolinones Enabled by Photo-Induced Radical Phosphorylation/Cyclization of Unactivated Alkenes

“…Step A: A 250 mL oven-dried round-bottom flask was charged with methyltriphenylphosphonium bromide (5.36 g, 15 mmol) and dry tetrahydrofuran (20 mL) under an argon atmosphere, followed by the addition of potassium tert -butoxide (1.68 g, 15 mmol) at 0 °C. The reaction mixture was allowed to warm to ambient temperature and stir for 30 min.…”

Rhodium(III)-Catalyzed Annulation Synthesis of Difluorinated Quinazolinone Derivatives Using an Amide Carbonyl as the Directing Group

“…The solvents were obtained by distillation before use. 1a , 2a , and the catalyst were prepared according to literature procedures. − …”

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C–C Bond Cleavage of Isatins

“…17 Synthesis of 3-Phenylquinazolin-4(3H)-one (6). The compound 6 was prepared according to the literature procedure 18 and purified by column chromatography (petroleum ether/ethyl acetate = 3:1) to give the product as a white solid: 62% yield, (138 mg); 1 H NMR (CDCl 3 , 400 MHz, ppm): δ = 8.38 (d, J = 8.0 Hz, 1H), 8.14 (s, 1H), 7.84−7.77 (m, 2H), 7.58−7.49 (m, 4H), 7.44 (d, J = 7.6 Hz, 2H); 13 C NMR (CDCl 3 , 100 MHz, ppm): δ = 160.7, 147.8, 146.1, 137.4, 134.6, 129.6, 129.1, 127.6, 127.6, 127.2, 127.0, 122.3. 18 Methyl 2-Aminobenzoate (2a).…”

“…The compound 6 was prepared according to the literature procedure 18 and purified by column chromatography (petroleum ether/ethyl acetate = 3:1) to give the product as a white solid: 62% yield, (138 mg); 1 H NMR (CDCl 3 , 400 MHz, ppm): δ = 8.38 (d, J = 8.0 Hz, 1H), 8.14 (s, 1H), 7.84−7.77 (m, 2H), 7.58−7.49 (m, 4H), 7.44 (d, J = 7.6 Hz, 2H); 13 C NMR (CDCl 3 , 100 MHz, ppm): δ = 160.7, 147.8, 146.1, 137.4, 134.6, 129.6, 129.1, 127.6, 127.6, 127.2, 127.0, 122.3. 18 Methyl 2-Aminobenzoate (2a). 4e The title compound was prepared according to the general working procedure A and purified by column chromatography (petroleum ether/ethyl acetate = 10:1) to give the product as a light yellow oil: 84% yield, (38 mg); 1 H NMR (CDCl 3 , 400 MHz, ppm): δ = 7.88 (d, J = 8.0 Hz, 1H), 7.29 (t, J = 8.4 Hz, 1H), 6.69−6.65 (m, 2H), 5.74 (br, 2H), 3.89 (s, 3H); 13 C NMR (CDCl 3 , 100 MHz, ppm): δ = 168.6, 150.4, 134.1, 131.2, 116.6, 116.2, 110.7, 51.5.…”