Synlett, Table of Contents Synlett 2020; 31(03): 275-279DOI: 10.1055/s-0037-1610740 letter © Georg Thieme Verlag Stuttgart · New YorkCopper-Catalyzed One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones from 2-Nitrobenzonitriles and Carbonyl Compounds Mediated by Diboronic Acid in Methanol–Water Qixing Liu , Yuebo Sui , Yin Zhang , Kaili Zhang , Yongsheng Chen , Haifeng Zhou ∗Recommend Article Abstract Buy Article All articles of this category § 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 Key wordscopper catalysis - diboronic acid - dihydroquinazolinones - carbonyl compounds - nitrobenzonitriles Full Text References References and Notes 1a Badolato M, Aiello F, Neamati N. RSC Adv. 2018; 8: 20894 1b Roopan SM, Khan FN, Jin JS, Kumar RS. Res. Chem. Intermed. 2011; 37: 919 1c Williams R, Niswender CM, Luo Q, Le U, Conn PJ, Lindsley CW. Bioorg. Med. Chem. Lett. 2009; 19: 962 1d Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893 2a Liu P, Deng DS, Wang L. J. Clust. Sci. 2018; 29: 1031 2b Sarfraz M, Sultana N, Rashid U, Akram MS, Sadiq A, Tariq MI. Bioorg. Chem. 2017; 70: 237 2c Huang G, Liu B, Teng MY, Chen Y. Lett. Org. Chem. 2016; 13: 453 2d Rahman M, Ling I, Abdullah N, Hashim R, Hajra A. RSC Adv. 2015; 5: 7755 2e Labade VB, Shinde PV, Shingare MS. Tetrahedron Lett. 2013; 54: 5778 2f Rostami A, Tavakoli A. Chin. Chem. Lett. 2011; 22: 1317 3a Luo Y, Wu Y, Wang Y, Sun H, Xie Z, Zhang W, Gao Z. 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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. 14a Yang L, Li J, Chai H, Lu H, Zhang Q, Shi D. Chin. J. Chem. 2013; 31: 443 14b Li J, Zhang L, Shi D, Li Q, Wang D, Wang C, Zhang Q, Zhang L, Fan Y. Synlett 2008; 233 14c Yang J, Shi D, Liu M, Zhang L, Zhang Q, Li J. Chin. J. Org. Chem. 2014; 34: 2424 Supplementary Material Supplementary Material Supporting Information
