Synthesis, Table of Contents Synthesis 2021; 53(06): 1103-1111DOI: 10.1055/s-0040-1706473 paper Facile and Mild Access to Fluorescent Ladder-Type Indolo[3,2-a]carbazoles via Cascade Annulation Shuangrong Liu , You Wu , Zhimin Ying , Feng Luo , En Chen , Wenteng Chen∗ , Yongping Yu∗ Recommend Article Abstract Buy Article All articles of this category Abstract A set of fluorescent ladder-type indolo[3,2-a]carbazoles were rationally developed via cascade annulation of indoles and nitroolefins under mild reaction conditions. Diverse functional groups were tolerated. Moreover, structure–photophysical properties relationships (SPPR) of indolo[3,2-a]carbazoles were observed to be simply tuned by changing the electronic nature of the peripheral substituents. Key words Key wordsfluorescence - ladder-type - indolo[3,2-a]carbazole - cascade annulation - mild reaction Full Text References References 1 Frederickson CK, Rose BD, Haley MM. Acc. Chem. Res. 2017; 50: 977 2a Hu L, Zhang G, Liu Y, Guo T, Shao L, Ying L. J. Mater. Chem. C. 2020; 8: 2160 2b Marlet S, Birau M, Wang ZY. Org. Lett. 2002; 4: 2157 3a Chang SJ, Liu X, Lu TT, Liu YY, Pan JQ, Jiang Y, Chu SQ, Lai WY, Huang W. J. Mater. Chem. C. 2017; 5: 6629 3b Fix AG, Deal PE, Vonnegut CL, Rose BD, Zakharov LN, Haley MM. Org. Lett. 2013; 15: 1362 4a Thirion D, Rault-Berthelot J, Vignau L, Poriel C. Org. Lett. 2011; 13: 4418 4b Hadizad T, Zhang J, Wang ZY, Gorjanc TC, Py C. Org. Lett. 2005; 7: 795 5 Lo YC, Ting HC, Li YZ, Li YH, Liu SW, Huang KW, Wong KT. Org. Chem. Front. 2017; 4: 675 6 Jiang ZQ, Wang TT, Wu FP, Lin JD, Liao LS. J. Mater. Chem. A. 2018; 6: 17256 7 Bebiche S, Cisneros-Perez PA, Mohammed-Brahim T, Harnois M, Rault-Berthelot J, Poriel C, Jacques E. Mater. Chem. Front. 2018; 2: 1631 8 Morgan MM, Nazari M, Pickl T, Rautiainen JM, Tuononen HM, Piers WE, Welch GC, Gelfand BS. Chem. Commun. 2019; 55: 11095 9 Zhang Y, Peng F, He R, Ying L, Yang W, Cao Y. New J. Chem. 2018; 42: 2750 10 Ebata H, Miyazaki E, Yamamoto T, Takimiya K. Org. Lett. 2007; 9: 4499 11 Kawaguchi K, Nakano K, Nozaki K. J. Org. Chem. 2007; 72: 5119 12a de Jong F, Daniels M, Vega-Castillo L, Kennes K, Martín C, de Miguel G, Cano M, Pérez-Morales M, Hofkens J, Dehaen W, der Auweraer MV. J. Phys. Chem. B 2019; 123: 1400 12b Zhang Y, Chen S, Zhang Y, Du H, Zhao J. Polymers 2019; 11: 1626 12c Panda S, Ansari MA, Mandal A, Lahiri GK. Chem. Asian J. 2019; 14: 4631 12d Kader T, Stöger B, Fröhlich J, Kautny P. Chemistry 2019; 25: 4412 12e Mula S, Leclerc N, Lévêque P, Retailleau P, Ulrich G. J. Org. Chem. 2018; 83: 14406 12f Zhao C, Schwartz T, Stöger B, White FJ, Chen J, Ma D, Fröhlich J, Kautny P. J. Mater. Chem. C 2018; 6: 9914 13 Tsuchimoto T, Matsubayashi H, Kaneko M, Nagase Y, Miyamura T, Shirakawa E. J. Am. Chem. Soc. 2008; 130: 15823 14 Janosik T, Bergman J. Tetrahedron 1999; 55: 2371 15 An YL, Yang ZH, Zhang HH, Zhao SY. Org. Lett. 2016; 18: 152 16a Sankar E, Raju P, Karunakaran J, Mohanakrishnan AK. J. Org. Chem. 2017; 82: 13583 16b González JF, Rocchi D, Tejero T, Merino P, Menéndez JC. J. Org. Chem. 2017; 82: 7492 16c Zhao CY, Li YK, Pang Y, Li JQ, Liang C, Su GF, Mo DL. Adv. Synth. Catal. 2018; 360: 1919 16d Zheng X, Lv L, Lu S, Wang W, Li Z. Org. Lett. 2014; 16: 5156 17 Huang P, Peng X, Hu D, Liao H, Tang S, Liu L. Org. Biomol. Chem. 2017; 15: 9622 18 Valentine RA, Whyte A, Awaga K, Robertson N. Tetrahedron Lett. 2012; 53: 657 19 Tang RY, Guo XK, Xiang JN, Li JH. J. Org. Chem. 2013; 78: 11163 20a Nair V, Nandialath V, Abhilash KG, Suresh E. Org. Biol. Chem. 2008; 6: 1738 20b Kazin NA, Demina NS, Irgashev RA, Zhilina EF, Rusinov GL. Tetrahedron 2019; 75: 4686 21 Dupeyre G, Lemoine P, Ainseba N, Michel S, Cachet X. Org. Biomol. Chem. 2011; 9: 7780 22 Chen W, Luo F, Wu Y, Cen J, Shao J, Yu Y. Org. Chem. Front. 2020; 7: 882 23 Lancianesi S, Palmieri A, Petrini M. Chem. Rev. 2014; 114: 7108 24 Padilha G, Iglesias BA, Back DF, Kaufman TS, Silveira CC. ChemistrySelect 2017; 2: 1297 Supplementary Material Supplementary Material Supporting Information
