Synthesis, Table of Contents Synthesis 2021; 53(23): 4495-4500DOI: 10.1055/a-1550-3451 paper Convenient Synthesis of Benzofuro[3,2-b]quinolines from 1-Azadienes and Arynes Qi Wang , Yan Wang , Shi-Kai Tian∗ Recommend Article Abstract Buy Article All articles of this category Abstract An efficient method has been developed for the synthesis of benzofuro[3,2-b]quinolines through tandem [4+2] cycloaddition/ aromatization under transition-metal-free conditions. A range of aurone-derived N-tosyl-1-azadienes smoothly reacted with arynes, generated in situ via fluoride ion-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates, delivering structurally diverse benzofuro[3,2-b]quinolines in moderate to good yields. Key words Key words1-azadienes - arynes - benzofuro[3,2-b]quinolines - aromatization - cycloaddition Full Text References References 1a Behforouz M, Ahmadian M. Tetrahedron 2000; 56: 5259 1b Groenendaal B, Ruijter E, Orru RV. A. Chem. Commun. 2008; 5474 1c Monbaliu J.-CM, Masschelein KG. R, Stevens CV. Chem. Soc. Rev. 2011; 40: 4708 1d Li J.-L, Liu T.-Y, Chen Y.-C. Acc. Chem. Res. 2012; 45: 1491 1e Cao M.-H, Green NJ, Xu S.-Z. Org. Biomol. Chem. 2017; 15: 3105 1f Skrzyńska A, Frankowski S, Albrecht Ł. Asian J. Org. Chem. 2020; 9: 1688 1g Yu S, Gao L, Lan H, Qian H, Yin Z, Shang Y. Chin. J. Org. Chem. 2020; 40: 2714 2a Stokes S, Bekkam M, Rupp M, Mead KT. Synlett 2012; 23: 389 2b Stokes S, Mead KT. Synth. Commun. 2013; 43: 2627 2c Kiran IN. C, Reddy RS, Chandraiah L, Xu H, Wang Z, He Y. J. Org. Chem. 2017; 82: 1823 For reviews on aryne chemistry, see: 3a Kitamura T. Aust. J. Chem. 2010; 63: 987 3b Gampe CM, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3766 ; Angew. Chem. 2012, 124, 3829 3c Tadross PM, Stoltz BM. Chem. Rev. 2012; 112: 3550 3d Bhunia A, Yetra SR, Biju AT. Chem. Soc. Rev. 2012; 41: 3140 3e Wu C, Shi F. Asian J. Org. Chem. 2013; 2: 116 3f Dubrovskiy AV, Markina NA, Larock RC. Org. Biomol. Chem. 2013; 11: 191 3g Bhojgude SS, Bhunia A, Biju AT. Acc. Chem. Res. 2016; 49: 1658 3h Shi J, Li L, Li Y. Chem. Rev. 2021; 121: 3892 4a Kempter G, Hirschberg S. Chem. Ber. 1965; 98: 419 4b Kempter G, Zänker P, Zürner H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967; 300: 829 4c Sunder S, Peet NP. J. Heterocycl. Chem. 1978; 15: 1379 4d Yamaguchi S, Tsuzuki K, Sannomiya Y, Oh-hira Y, Kawase Y. J. Heterocycl. Chem. 1989; 26: 285 4e Malecki N, Carato P, Rigo B, Goossens J.-F, Houssin R, Bailly C, Hénichart J.-P. Bioorg. Med. Chem. 2004; 12: 641 4f Zhu XY, Mardenborough LG, Li S, Khan A, Zhang W, Fan P, Jacob M, Khan S, Walker L, Ablordeppey SY. Bioorg. Med. Chem. 2007; 15: 686 5 Yang S.-W, A.-Kader M, Malone S, Werkhoven MC. M, Wisse JH, Bursuker I, Neddermann K, Fairchild C, Raventos-Suarez C, Menendez AT, Lane K, Kingston DG. I. J. Nat. Prod. 1999; 62: 976 6 Zheng Y.-Y, Du R.-L, Cai S.-Y, Liu Z.-H, Fang Z.-Y, Liu T, So L.-Y, Lu Y.-J, Sun N, Wong K.-Y. Front. Microbiol. 2018; 9: 1937 7a Zhao M, Kamada T, Takeuchi A, Nishioka H, Kuroda T, Takeuchi Y. Bioorg. Med. Chem. Lett. 2015; 25: 5551 7b Sun N, Du R.-L, Zheng Y.-Y, Huang B.-H, Guo Q, Zhang R.-F, Wong K.-Y, Lu Y.-J. Eur. J. Med. Chem. 2017; 135: 1 8a Peng W, Sun Z-Y, Zhang Q, Cheng S.-Q, Wang S.-K, Wang X-N, Kuang G.-T, Su X.-X, Tan J.-H, Huang Z.-S, Ou T.-M. J. Med. Chem. 2018; 61: 6629 8b Qin Q.-P, Wei Z-Z, Wang Z.-F, Huang X.-L, Tan M.-X, Zou H-H, Liang H. Chem. Commun. 2020; 56: 3999 8c Qin L-Q, Liang C.-J, Zhou Z, Qin Q-P, Wei Z.-Z, Tan M.-X, Liang H. Bioorg. Med. Chem. 2021; 30: 115948 9a Ferles M, Jančar P, Kocián O. Collect. Czech. Chem. Commun. 1979; 44: 2672 9b Grignon-Dubois M, Fialeix M, Rezzonico B. Can. J. Chem. 1990; 68: 2153 9c Neochoritis CG, Eleftheriadis N, Tsiantou A, Stephanidou-Stephanatou J, Tsoleridis CA. Synlett 2013; 24: 2768 10 CCDC 2030789 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures. 11a Rong Z.-Q, Wang M, Chow CH. E, Zhao Y. Chem. Eur. J. 2016; 22: 9483 11b Fan T, Zhang Z.-J, Zhang Y.-C, Song J. Org. Lett. 2019; 21: 7897 11c Li X, Yan J, Qin J, Lin S, Chen W, Zhan R, Huang H. J. Org. Chem. 2019; 84: 8035 11d Liu K, Yang J, Li X. Org. Lett. 2021; 23: 826 Supplementary Material Supplementary Material Supporting Information
