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Synlett 2020; 31(03): 275-279
DOI: 10.1055/s-0037-1610740
DOI: 10.1055/s-0037-1610740
letter
Copper-Catalyzed One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones from 2-Nitrobenzonitriles and Carbonyl Compounds Mediated by Diboronic Acid in Methanol–Water
Natural Science Foundation of Hubei Province of China (2018CFB241)Further Information
Publication History
Received: 29 September 2019
Accepted after revision: 02 December 2019
Publication Date:
12 December 2019 (online)
§ The authors contributed equally.
Abstract
A copper-catalyzed one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones with diboronic acid as a reductant in an aqueous medium is described. Various 2,3-dihydroquinazolin-4(1H)-ones were prepared with good functional-group tolerance in good yields under mild conditions from readily available 2-nitrobenzonitriles and various carbonyl compounds.
Key words
copper catalysis - diboronic acid - dihydroquinazolinones - carbonyl compounds - nitrobenzonitrilesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610740.
- Supporting Information
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- 13 2-Phenyl-2,3-dihydroquinazolin-4(1H)-one (3a); Typical Procedure A 10-mL tube was charged with 2-nitrobenzonitrile (1; 0.5 mmol), benzaldehyde (2a; 0.6 mmol), B2(OH)4 (2.5 mmol), CuCl (0.1 mmol), H2O (1 mL), and MeOH (1 mL), and the mixture was stirred at 60 °C for 3 h. The mixture was then extracted with EtOAc (3 × 5 mL) and the organic layers were combined, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography [silica gel, PE–EtOAc (5:1)] to give a white solid; yield: 101.9 mg (91%); mp 224–225 °C. 1H NMR (400 MHz, CDCl3): δ = 7.99 (d, J = 7.2 Hz, 1 H), 7.66–7.63 (m, 2 H), 7.52–7.49 (m, 3 H), 7.39 (dt, J 1 = 7.6 Hz, J 2 = 1.6 Hz , 1 H), 6.95 (t, J = 7.6 Hz, 1 H), 6.72 (d, J = 8.0 Hz, 1 H), 5.95 (s, 1 H), 5.80 (s, 1 H), 4.44 (s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 164.7, 147.2, 138.6, 134.0, 130.2, 129.2, 128.8, 127.4, 119.7, 115.7, 114.6, 69.1.