Synlett, Table of Contents Synlett 2022; 33(06): 563-568DOI: 10.1055/a-1729-6586 letter Copper(I) Iodide Promoted [3+2]-Cycloaddition/Oxidation to Construct Pyrrolo[2,1-a]isoquinolinoquinones from Naphthoquinones and Tetrahydroisoquinolines Zihua Yu , Xue Tang , Chenxi Huang , Yehan Shang , Qing Ye , Liang Han , Yujin Li ∗ Recommend Article Abstract Buy Article All articles of this category Abstract A copper-catalyzed, three-component, one-pot, 1,3-dipole cycloaddition/oxidation has been developed to construct pyrrolo[2,1-a]isoquinolinoquinone derivatives, with environmentally friendly oxygen as the oxidant. The pyrrolo[2,1-a]isoquinolinoquinone products were obtained from naturally available tetrahydroisoquinolines, 1,4-naphthoquinones, and benzaldehydes in medium yields. Key words Key wordspyrroloisoquinolinoquinones - copper catalysis - tetrahydroisoquinolines - [3+2]-cycloaddition - oxidation - multicomponent reaction Full Text References References and Notes 1a Naskar S, Banerjee M, Hazra A, Mondal S, Maity A, Paira R, Sahu KB, Saha P, Banerjee S, Mondal NB. Tetrahedron Lett. 2011; 52: 1527 1b Voskressensky LG, Borisova TN, Matveeva MD, Khrustalev VN, Titov AA, Aksenov AV, Dyachenko SV, Varlamov AV. Tetrahedron Lett. 2017; 58: 877 1c Borthakur S, Sarma B, Gogoi S. Org. Lett. 2019; 21: 7878 2a Davis RA, Carroll AR, Pierens GK, Quinn RJ. J. Nat. Prod. 1999; 62: 419 2b Dittrich N, Pilkington LI, Leung E, Barker D. Tetrahedron 2017; 73: 1881 3 Colligs V, Hansen SP, Imbri D, Seo E.-J, Kadioglu O, Efferth T, Opatz T. Bioorg. Med. Chem. 2017; 25: 6137 4 Li L, Jiao Y, Jin T, Sun H, Li S, Jin C, Hu S, Ji J, Xiang L. Life Sci. 2017; 191: 211 5 Zhang F, Simpkins NS, Blake AJ. Org. Biomol. Chem. 2009; 7: 1963 6a Wu TR, Chong JM. J. Am. Chem. 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Purification of the crude product by column chromatography [silica gel, CH2Cl2–PE (1:1)] gave a yellow solid; yield: 0.1378 g (73%); mp 240–242 °C. 1H NMR (500 MHz, CDCl3): δ = 9.09 (d, J = 7.8 Hz, 1 H), 8.30 (dd, J = 7.6, 1.1 Hz, 1 H), 8.13 (dd, J = 7.5, 1.2 Hz, 1 H), 7.64 (m, 2 H), 7.54–7.47 (m, 5 H), 7.44 (t, J = 7.4 Hz, 1 H), 7.33 (m, 1 H), 7.22 (t, J = 7.0 Hz, 1 H), 3.95–3.88 (m, 2 H), 2.97 (t, J = 6.5 Hz, 2 H). 13C NMR (125 MHz, CDCl3): δ = 180.14, 180.10, 137.86, 136.38, 136.24, 135.30, 134.31, 133.79, 132.91, 132.72, 130.48 (2 C), 129.52, 129.48, 128.61, 128.42 (2 C), 127.42, 127.34, 127.25, 127.11, 126.36, 119.53, 117.48, 42.29, 29.54. HRMS (ESI): m/z [M + Na]+ calcd for C26H17NNaO2: 398.1157; found: 398.1149. Supplementary Material Supplementary Material Supporting Information
