Synthesis of Methylene Bridged Bis-pyrrolo[3,2-c]carbazoles via an Unusual Vilsmeier–Haack Product of N-Ethylcarbazole

References

• F. F. Zhang, L. L. Gan, and C. H. Zhou, “Synthesis, Antibacterial and Antifungal Activities of Some Carbazole Derivatives,” Bioorganıc and Medicinal Chemistry Letter 20 (2010): 1881–4. doi:10.1016/j.bmcl.2010.01.159.
   PubMed Web of Science ®Google Scholar
• Y. Li and W. Gao, “Synthesis of 3-(Quinolin-2-yl)- and 3,6-Bis(quinolin-2-yl)-9H-Carbazoles,” Beilstein Journal of Organic Chemistry 6 (2010): 966–72. doi:10.3762/bjoc.6.108.
   PubMed Web of Science ®Google Scholar
• H. J. Knölker and K. R. Reddy, “Isolation and Synthesis of Biologically Active Carbazole Alkaloids,” Chemical Review 102 (2002): 4303–427. doi:10.1021/cr020059j.
   PubMed Web of Science ®Google Scholar
• M. M. Rahman and A. I. Gray, “A Benzoisofuranone Derivative and Carbazole Alkaloids from Murraya koenigii and their Antimicrobial Activity,” Phytochemistry 66 (2005): 1601–6. doi:10.1016/j.phytochem.2005.05.001.
   PubMed Web of Science ®Google Scholar
• G. Bringmann, A. Ledermann, J. Holenz, M. T. Kao, U. Busse, H. G. Wu, and G. Francois, “Antiplasmodial Activity of Mono- and Dimeric Carbazoles,” Planta Medica 64 (1998): 54–57. doi:10.1055/s-2006-957366.
   PubMed Web of Science ®Google Scholar
• S. Tasler and G. Bringmann, “Biarylic Biscarbazole Alkaloids: Occurrence, Stereochemistry, Synthesis, and Bioactivity,” The Chemical Record 2 (2002): 114–27. doi:10.1002/tcr.10014.
   Web of Science ®Google Scholar
• G. Li, X. Zhou, P. Yang, Y. Jian, T. Deng, H. Shen, and Y. Bao, “Synthesis of a Novel Methylene-Bridged Biscarbazole Derivative and Evaluation of its DNA and Nucleotide Binding Properties,” Tetrahedron Letter 55 (2014): 7054–9. doi:10.1016/j.tetlet.2014.10.134.
   Web of Science ®Google Scholar
• G. Bringmann and S. Tasler, “Synthesis of Methylene-Bridged Binary Carbazole Alkaloids and a Related Tricarbazole,” Tetrahedron 57 (2001): 2337–43. doi:10.1016/S0040-4020(01)00104-1.
   Web of Science ®Google Scholar
• C. Börger, W. A. Schmid, and H. Knölker, “First Total Syntheses of Chrestifoline-B and (±)-Chrestifoline-C, and Improved Synthetic Routes to Bismurrayafoline-A, Bismurrayafolinol and Chrestifoline-D,” Journal of Organic and Biomolecular. Chemistry 12 (2014): 3831–383. doi:10.1039/C4OB00609G.
   PubMed Web of Science ®Google Scholar
• D. A. Horton, G. T. Bourne, and M. L. Smythe, “The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures,” Chemical Reviews 103 (2003): 893–930. doi:10.1021/cr020033s.
   PubMed Web of Science ®Google Scholar
• C. Gil and S. Brase, “Solid-Phase Synthesis of Biologically Active Benzoannelated Nitrogen Heterocycles: An Update,” Journal of Combinatorial Chemstry 11 (2009): 175–97. doi:10.1021/cc800102t.
   PubMed Web of Science ®Google Scholar
• R. Akue-Gedu, E. Rossignol, S. Azzaro, S. Knapp, P. Filippakopoulos, A. N. Bullock, J. Bain, P. Cohen, M. Prudhomme, F. Anizon, and P. Moreau, “Synthesis, Kinase Inhibitory Potencies, and in Vitro Antiproliferative Evaluation of New Pim Kinase Inhibitors,” Journal of Medicinal Chemistry 52 (2009): 6369–81. doi:10.1021/jm901018f.
   PubMed Web of Science ®Google Scholar
• B. Hugon, F. Anizon, C. Bailly, R. M. Golsteyn, A. Pierre, S. L. J. Hickman, and B. P. M. Prudhomme, “Synthesis and Biological Activities of Isogranulatimide Analogues,” Bioorganic & Medicinal Chemistry 15 (2007): 5965–80. doi:10.1016/j.bmc.2007.05.073.
   PubMed Web of Science ®Google Scholar
• N. Viji and R. Nagarajan, “Zinc Triflate Catalyzed Regioselective Synthesis of Pyrrolo[2,3 c]carbazoles via Heteroannulation,” RSC Advances 2 (2012): 10544–9. doi:10.1039/c2ra21735j.
   Web of Science ®Google Scholar
• M. A. Fousteris, A. Papakyriakou, A. Koutsourea, M. Manioudaki, E. Lampropoulou, Evangelia Papadimitriou, Georgios A. Spyroulias, and S. S. Nikolaropoulos, “Pyrrolo[2,3-a]carbazoles as Potential Cyclin Dependent Kinase 1 (CDK1) Inhibitors. Synthesis, Biological Evaluation, and Binding Mode through Docking Simulations,” Journal of Medicinal Chemistry 51 (2008): 1048–52. doi:10.1021/jm0700666.
   PubMed Web of Science ®Google Scholar
• L. William, C. S. Gelbaum, L. Gelbaum, P. Pollet, K. W. Richman, W. DuBay, J. D. Butler, G. Wells, and C. L. Liotta, “Indoles via Knoevenagel–Hemetsberger Reaction Sequence,” RSC Advances 3 (2013): 13232–42. doi:10.1039/c3ra42296h.
   Web of Science ®Google Scholar
• C. Ayats, R. Soley, F. Albericio, and M. Alvarez, “Synthesis of the Pyrrolo[2,3-c]carbazole Core of the Dictyodendrins,” Journal of Organic and Biomoecular Chemistry 7 (2009): 860–2. doi:10.1039/b822933n.
   PubMed Web of Science ®Google Scholar
• H. Hemetsberger, D. Knittel, and H. Enazide Weidmann, “3. Mitt.: Thermolyse von α-Azidozimtestern; Synthese von Indolderivaten,” Monatshefte fur Chemie 101 (1970): 161–5. doi:10.1007/BF00907536.
   Google Scholar
• H. Hemetsberger, D. Knittel, and H. Weidmann, “Synthese von α Azidozimtsäureestern,” Monatshefte fur Chemie 100 (1969): 1599–603. doi:10.1007/BF00900176.
   Google Scholar
• H. Hemetsberger, D. Knittel, and H. Weidmann, “Synthese und Thermolyse von α-Azidoacrylestern,” Monatshefte fur Chemie 103 (1972): 194–204. doi:10.1007/BF00912944.
   Google Scholar
• M. Bingul, B. D. Cheung, N. Kumar, and StC. D. Black, “Synthesis of Symmetrical and Unsymmetrical Diindolylmethanes via Acid-Catalysed Electrophilic Substitution Reactions,” Tetrahedron 70 (2014): 7363–9. doi:10.1016/j.tet.2014.06.087.
   Web of Science ®Google Scholar
• T. Wada, Y. Zhang, M. Yamakado, and H. Sasabe, “Linear and Nonlinear Optical Properties of Carbazole-Containing Polymers,” Molecular Crystal and Liquid Crystals 227 (1993): 85–92. doi:10.1080/10587259308030963.
   Web of Science ®Google Scholar
• H. Kandemir and I. F. Sengul, “Facile Synthesis of Some 3-(Benzimidazol-2-yl)- and 3,6-Di(Benzimidazol-2-yl)-9-ethyl-9H-carbazoles,” Synthetic Communication 22 (2015): 2583–91. doi:10.1080/00397911.2015.1094819.
   Google Scholar
• C. M. Marson, “Reactions of Carbonyl Compounds with (Monohalo) Methyleniminium Salts (Vilsmeier Reagents),” Tetrahedron 48 (1992): 3659–726. doi:10.1016/S0040-4020(01)92263-X.
   Web of Science ®Google Scholar
• G. Johnes and S. P. Stanforth, “Vilsmeier Reaction. 2. Reactions with Compounds Other Than Fully Conjugated Carbocycles and Heterocycles,” Organic Reactions 56 (2000): 355–9.
   Google Scholar
• R. Budreckiene, G. Buika, J. Grazulevicius, V. Jankauskas, and B. Staniskiene, “Vinyloxyethyl-Substituted Carbazole-Based Hydrazone and its Adducts with Diol and Dithiol as Glass-Forming Hole Transport Materials,” Journal of Photochemistry Photobiology A 181 (2006): 257–62. doi:10.1016/j.jphotochem.2005.12.006.
   Web of Science ®Google Scholar
• L. Yu, L. Li, and X. Fei, “Spectral Study, Stability and Protein Labeling of two Carbazole–Benzothiazole Derivatives,” Journal of Luminescene 149 (2014): 28–34. doi:10.1016/j.jlumin.2013.12.057.
   Web of Science ®Google Scholar
• I. F. Sengul, K. Wood, P. K. Bowyer, M. Bhadbhade, Rui Chen, N. Kumar, and D. StC. Black, “Synthesis of New Di-(3-indolyl)arenes,” Tetrahedron 68 (2012): 7429–34. doi:10.1016/j.tet.2012.06.074.
   Web of Science ®Google Scholar
• H. Kandemir, I. F. Sengul, N. Kumar, and D. StC. Black, “Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles,” Australian Journal Chemistry 70 (2017): 1196–201. doi:10.1071/CH17264.
   Web of Science ®Google Scholar
• CCDC 1420007 (for compound 4) and 1420008 (for compound 10b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
   Google Scholar
• I. F Sengul, E. Astarci, and H. Kandemir, “Synthesis of Novel Pyrrolo[3,2-c]carbazole and Dipyrrolo[3,2-c:2′,3′-g]carbazole Derivatives,” Synlett 27 (2016): 1277–81. doi:10.1055/s-0035-1560601.
   Web of Science ®Google Scholar