Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers

References

• (a) McCallion, G. D. An Efficient Synthesis and Substitution of 3-Aroyl-2-bromobenzo[b]furans. Curr. Org. Chem. 1999, 3, 67. DOI: 10.1021/jo701656z.
   Web of Science ®Google Scholar
  (b) Kadieva, M. G.; Oganesyan, E. T. Methods for the Synthesis of Benzofuran Derivatives (Review). Chem. Heterocycl. Compd. 1997, 33, 1245. DOI: 10.1007/BF02320323.
   Google Scholar
  (c) Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds. Comp. Heterocycl. Chem. II. 1996, 2, 259. DOI: 10.1021/jm9706123.
   Google Scholar
  (d) Dean, F. M.; Sargent, M. V. Furans and their Benzo Derivatives. Comp. Heterocycl. Chem. 1984, 4, 531. DOI: 10.1016/B978-008096519-2.00060-6.
   Google Scholar
• (a) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. Five-membered ring systems: furans and benzofurans. Prog. Heterocycl. Chem. 2008, 19, 176–207. DOI: 10.1016/S0959-6380(08)80009-8.
   Google Scholar
  (b) Gribble, G. W.; Joule, J. A., Eds. Oxford: Elsevier, 2008, pp 176; and previous volumes in the series. For recent work on benzofurans of pharmacological interest, see.
   Google Scholar
  (c) Carlsson, B.; Singh, B. N.; Temciuc, M.; Nilsson, S.; Li, Y. L.; Mellin, C.; Malm, J. Synthesis and Preliminary Characterization of a Novel Antiarrhythmic Compound (KB130015) with an Improved Toxicity Profile Compared with Amiodarone. J. Med. Chem. 2002, 45, 623. DOI: 10.1021/jm001126%2B. DOI: 10.1021/jm001126+.
   PubMed Web of Science ®Google Scholar
  (d) Flynn, B. L.; Hamel, E.; Jung, M. K. One-Pot Synthesis of Benzo[b]Furan and Indole Inhibitors of Tubulin Polymerization. J. Med. Chem. 2002, 45, 2670. DOI: 10.1021/jm020077t.
   PubMedGoogle Scholar
• Erber, S.; Ringshandl, R.; von Angerer, E. 2-Phenylbenzo[b]Furans: relationship between Structure, Estrogen Receptor Affinity and Cytostatic Activity against Mammary Tumor Cells. Anti-Cancer Drug Des. 1991, 6, 417.
   PubMedGoogle Scholar
• Malamas, M. S.; Sredy, J.; Moxham, C.; Katz, A.; Xu, W. X.; McDevitt, R.; Adebayo, F. O.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; et al. Novel Benzofuran and Benzothiophene Biphenyls as Inhibitors of Protein Tyrosine Phosphatase 1B with Antihyperglycemic Properties. J. Med. Chem. 2000, 43, 1293. DOI: 10.1021/jm990560c.
   PubMed Web of Science ®Google Scholar
• Watanabe, Y.; Yoshiwara, H.; Kanao, M. Syntheses of 4-(Benzo[b]Furan-2 or 3-yl)- and 4-(Benzo[b]-Thiophen-3-yl)Piperidines with 5-HT 2 Antagonist Activity. J. Heterocycl. Chem. 1993, 30, 445. DOI: 10.1002/jhet.5570300228.
   Web of Science ®Google Scholar
• (a) McAllister, G. D.; Hartley, R. C.; Dawson, M. J.; Knaggs, A. R. Total Synthesis of Moracin C. J. Chem. Soc, Perkin Trans. 1 1998, 20, 3453. DOI: 10.1039/a805026k.
   Google Scholar
  (b) Dounya, S.; Van de Poll-Franse, L.; Pauline, V.; Myrthe, P. P.; Herk-Suke, V.; Susanne, S.; Nina, R.; Trine, H.; Susanne, D.; Johan, D. J. Breast Cancer Res. Treat. 2017, 166(1), 259–266. DOI: 10.1007/s10549-017-4387-1.
   Google Scholar
  (c) Cermakova, P.; Johnell, K.; Fastbom, J.; Garcia-Ptacek, S.; Lund, L. H.; Winblad, B.; Eriksdotter, M.; Religa, D. Cardiovascular Diseases in ∼30,000 Patients in the Swedish Dementia Registry. JAD. 2015, 48, 949–958. DOI: 10.3233/JAD-150499.
   Google Scholar
  (d) Xiaohua, L.; Dalin, S.; Sean, X. L. Link between Type 2 Diabetes and Alzheimer's Disease: From Epidemiology to Mechanism and Treatment. Clin. Interv. Aging. 2015, 10, 549–560. DOI: 10.2147/CIA.S74042.
   PubMed Web of Science ®Google Scholar
  (e) Chun-Ting, L.; Bei-Yu, W.; Chiang, H.; Wang, L. Y.; Yan-Yuh, L.; Tsu-Kung, L.; Pao-Yen, L.; Wu-Fu, C.; Jen-Huai, C.; Sheng-Feng, H.; et al. Decreased Risk of Dementia in Migraine Patients with Traditional Chinese Medicine Use: A Population-Based Cohort Study. Onco Target. 2017, 8, 79680–79692. DOI: 10.18632/oncotarget.19094.
   Google Scholar
• (a) Piloto, A. M.; Fonseca, A. S. C.; Costa, S. P. G.; Gonçalves, M. S. T. Carboxylic Fused Furans for Amino Acid Fluorescent Labelling. Tetrahedron. 2006, 62, 9258. DOI: 10.1016/j.tet.2006.07.003.
   Web of Science ®Google Scholar
  (b) Piloto, A. M.; Costa, S. P. G.; Gonçalves, M. S. T. A Naphtho[2,1-b]Furan as a New Fluorescent Label: synthesis and Spectral Characterisation. Tetrahedron Lett. 2005, 46, 4757. DOI: 10.1016/j.tetlet.2005.05.035.
   Web of Science ®Google Scholar
• (a) Babu, V. H.; Kumar, P. S.; Srinivasan, K. K.; Bhat, G. V. Synthesis, antitumor and antibacterial activities of certain substituted pyrimidines bearing benzofuran. Indian J. Pharm. Sci. 2004, 66, 647.
   Google Scholar
  (b) Hayakawa, I.; Shioya, R.; Agatsuma, T.; Furukawa, H.; Sugano, Y. Thienopyridine and Benzofuran Derivatives as Potent anti-Tumor Agents Possessing Different Structure–Activity Relationships. Bioorg. Med. Chem. Lett. 2004, 14, 3411. DOI: 10.1016/j.bmcl.2004.04.079.
   PubMed Web of Science ®Google Scholar
• Abdel-Kader, M. S. Phenolic Constituents of Ononis Vaginalis Roots. Planta Med. 2001, 67, 388. DOI: 10.1055/s-2001-14325.
   PubMed Web of Science ®Google Scholar
• Rahim, R. T.; Meissler, J. J., Jr.; Cowan, A.; Rogers, T. J.; Geller, E. B.; Gaughan, J.; Adler, M. W.; Eisenstein, T. K. Administration of mu-, Kappa- or delta2-Receptor Agonists via Osmotic Minipumps Suppresses Murine Splenic Antibody Responses. Internat. Immunopharmacol. 2001, 1, 2001. DOI: 10.1016/S1567-5769(01)00128-X.
   PubMed Web of Science ®Google Scholar
• (a) Frahm, A. W.; Muangnoicharoen, N. Arylbenzofurans from Dalbergia parviflora. Phytochem. 1981, 20, 291. DOI: 10.1016/0031-9422(81)85109-6.
   Web of Science ®Google Scholar
  (b) For a synthesis, see: Mukherjee, S. K.; Walia, S.; Kulshrestha, S. K. Photochemistry of latifolin and some related compounds.Tetrahedron. 1986, 42, 4817. DOI: 10.1016/S0040-4020(01)82062-7.
   Web of Science ®Google Scholar
• Shirota, O.; Pathak, V.; Sekita, S.; Satake, M.; Nagashima, Y.; Hirayama, Y.; Hakamata, Y.; Hayashi, T. Phenolic Constituents from Dalbergiacochinchinensis. J. Nat. Prod. 2003, 66, 1128. DOI: 10.1021/np0300683.
   PubMed Web of Science ®Google Scholar
• (a) Mustafa, A. In Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1974; Vol. 29, pp 1–514.
   Google Scholar
  (b) Mustafa, A. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, pp 259.
   Google Scholar
• (a) Nicolaou, K. C.; Snyder, S. A.; Bigot, A.; Pfefferkorn, J. A. Solution and Solid-Phase Synthesis of Functionalized 3-Arylbenzofurans by a Novel Cyclofragmentation – Release Pathway. J. Angew. Chem. Int. Ed. 2000, 39, 1093. DOI: 10.1002/1521-3773(20001002)39. DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1093::AID-ANIE1093>3.0.CO;2-S.
   PubMed Web of Science ®Google Scholar
  (b) Habermann, J.; Ley, S. V.; Smits, R. Three-Step Synthesis of an Array of Substituted Benzofurans Using Polymer-Supported Reagents. J. Chem. Soc, Perkin Trans. 1. 1999, 17, 2421. DOI: 10.1039/a904384e.
   Google Scholar
• Larock, R. C.; Stinn, D. E. Synthesis of Benzofurans via Palladium-Promoted Cyclization of Ortho-Substituted Aryl Allyl Ethers. Tetrahedron Lett. 1988, 29, 4687. DOI: 10.1016/S0040-4039(00)80581-X.
   Google Scholar
• Tae, J.; Kim, K. O. Synthesis of 2,3-Disubstituted Benzofurans from ortho -Acylphenols. Synthesis. 2005, 2005, 387. DOI: 10.1055/s-2004-834951.
   Google Scholar
• (a) Twyman, L. J.; Allsop, D. A Short Synthesis of the β-Amyloid (Aβ) Aggregation Inhibitor 3-p-Toluoyl-2-[4′-(3-Diethylaminopropoxy)-Phenyl]-Benzofuran. Tetrahedron Lett. 1999, 40, 9383. DOI: 10.1016/S0040-4039(99)02030-4.
   Web of Science ®Google Scholar
  (b) Ziegert, R. E.; Torang, J.; Knepper, K.; Brase, S. The Recent Impact of Solid-Phase Synthesis on Medicinally Relevant Benzoannelated Oxygen Heterocycles. J. Comb. Chem. 2005, 7, 147. DOI: 10.1021/cc049879v.
   PubMed Web of Science ®Google Scholar
  (c) Zeni, G.; Larock, R. C. Synthesis of Heterocycles via Palladium-Catalyzed Oxidative Addition. Chem. Rev. 2006, 106, 4644. DOI: 10.1021/cr0683966.
   PubMed Web of Science ®Google Scholar
  (d) Boswell, D. E.; Landis, P. S.; Givens, E. N.; Venuto, P. B. Catalytic Synthesis of Benzofuran. Ind. Eng. Chem. Prod. Res. Dev. 1968, 7, 215. DOI: 10.1021/i360027a012.
   Google Scholar
  (e) Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. Effect of Alteration of the Heterocyclic Nucleus of Indolactam V on Its Isoform Selectivity for PKC. Palladium-Catalyzed Route to Benzofuran Analogs of ILV. J. Am. Chem. Soc. 1995, 117, 6666. DOI: 10.1021/ja00130a003.
   Web of Science ®Google Scholar
  (f) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Gold Catalysis: On the Phenol Synthesis. Org. Lett. 2001, 3, 3769. DOI: 10.1021/ol016734d.
   PubMed Web of Science ®Google Scholar
  (g) Carril, M.; SanMartin, R.; Tellitu, I.; Dominguez, E. On-Water Chemistry: Copper-Catalyzed Straightforward Synthesis of Benzo[b]Furan Derivatives in Neat Water. Org. Lett. 2006, 8, 1467. DOI: 10.1021/ol060274c.
   PubMed Web of Science ®Google Scholar
• Yang, L. Y.; Chang, C. F.; Huang, Y. C.; Lee, Y. J.; Hu, C. C.; Tseng, T. H. The First Total Synthesis of Kynapcin-24 by Palladium Catalysis. Synthesis. 2009, 7, 1175. DOI: 10.1055/s-0028-1087998.
   Web of Science ®Google Scholar
• (a) Kim, S. I.; Park, I. H.; Song, K. S. Kynapcin-13 and -28, New Benzofuran Prolyl Endopeptidase. Inhibitors from Polyozellus multiplex. J. Antibiot. 2002, 7, 623. DOI: 10.1002/chin.200301211.
   Google Scholar
  (b) Song, K. S.; Raskin, I. A Prolyl Endopeptidase-Inhibiting Benzofuran Dimer from Polyozellusmultiflex. J. Nat. Prod. 2002, 65, 76. DOI: 10.1021/np010194b.
   PubMed Web of Science ®Google Scholar
• Bakunova, S. M.; Bakunov, S. A.; Wenzler, T.; Barszcz, T.; Werbovetz, K. A.; Brun, R.; Hall, J. E.; Tidwell, R. R. Synthesis and in Vitro Antiprotozoal Activity of Bisbenzofuran Cations. J. Med. Chem. 2007, 50, 5807. DOI: 10.1021/jm0708634.
   PubMedGoogle Scholar
• Kirilmis, C.; Koca, M.; Çukurovali, A.; Ahmedzade, M.; Kazaz, C. Synthesis, Reactivity and Biological Activity of Novel Bisbenzofuran-2-yl-Methanone Derivatives. Molecules. 2005, 10, 1399. DOI: 10.3390/10111399.
   PubMed Web of Science ®Google Scholar
• Janosik, T.; Bergman, J.; Stensland, B.; Stålhandske, C. Thionation of Bisindole Derivatives with P4S10 or Elemental Sulfur. J. Chem. Soc, Perkin Trans. 1. 2002, 0, 330. DOI: 10.1039/b109840c.
   Google Scholar
• Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. New Class of Chiral Diphosphine Ligands for Highly Efficient Transition Metal-Catalyzed Stereoselective Reactions: The Bis(Diphenylphosphino) Five-Membered Biheteroaryls. J. Org. Chem. 1996, 61, 6244. DOI: 10.1021/jo960211f.
   PubMed Web of Science ®Google Scholar
• (a) Gribble, G. W.; Berthel, S. J. In: Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed. Elsevier: New York, 1993; Vol. 12, pp 365.
   Google Scholar
  (b) Pindur, U.; Kim, Y. S.; Mehrabani, F. Advances in Indolo[2,3-a]Carbazole Chemistry: Design and Synthesis of Protein Kinase C and Topoisomerase I Inhibitors. Curr. Med. Chem. 1999, 6, 29. DOI: 10.1002/chin.199918300.
   PubMed Web of Science ®Google Scholar
  (c) Ito, S. A Chemist's View of Melanogenesis. Pigment Cell Res. 2003, 16, 230. DOI: 10.1034/j.1600-0749.2003.00037.x.
   PubMedGoogle Scholar
  (d) Lather, V.; Kristam, R.; Saini, J. S.; Kristam, R.; Karthikeyan, N. A.; Balaji, V. N. QSAR Models for Prediction of Glycogen Synthase Kinase‐3β Inhibitory Activity of Indirubin Derivatives. QSAR Comb. Sci. 2008, 27, 718. DOI: 10.1002/qsar.200730052.
   Google Scholar
• (a) Greci, L.; Tommasi, G.; Astolfi, P.; Petrucci, R.; Marrosu, G.; Trazza, A.; Sgarabotto, P.; Righi, L. Radical cations: reactions of 2-phenylindole with aromatic amines under anodic oxidation. β-Scission of an amino alkoxy radical. J. Chem. Soc, Perkin Trans. 2. 2000, 2, 1749. DOI: 10.1039/a909035e.
   Google Scholar
  (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Palladium-Catalyzed Reaction of o -Alkynyltrifluoroacetanilides with 1-Bromoalkynes. An Approach to 2-Substituted 3-Alkynylindoles and 2-Substituted 3-Acylindoles. J. Org. Chem. 2005, 70, 6213. DOI: 10.1021/jo050517z.
   PubMed Web of Science ®Google Scholar
  (c) Cacchi, S.; Fabrizi, G.; Lamba, D.; Marinelli, F.; Parisi, L. M. 2-Substituted 3-Aryl- and 3-Heteroarylindoles by the Palladium-Catalyzed Reaction of o-Trifluoroacetanilides with Aryl Bromides and Triflates. Synthesis. 2003, 5, 728. DOI: 10.1055/s-2003-38079.
   Google Scholar
• Desarbre, E.; Bergman, J. Synthesis of Symmetric and Non-Symmetric Indolo[2,3-c]Carbazole Derivatives: preparation of Indolo[2,3-c]Pyrrolo[3,4-a]Carbazoles. J. Chem. Soc, Perkin Trans. 1. 1998, 2009. DOI: 10.1039/a802852d.
   Google Scholar
• Duong, H. A.; Chua, S.; Huleatt, P. B.; Chai, C. L. L. Synthesis of Biindolyls via Palladium-Catalyzed Reactions. J. Org. Chem. 2008, 73, 9177. DOI: 10.1021/jo801846b.
   PubMed Web of Science ®Google Scholar
• (a) Sart, D. R.; Fagnou, K. The Catalytic Cross-Coupling of Unactivated Arenes. Science. 2007, 316, 1172. DOI: 10.1126/science.1141956.
   PubMed Web of Science ®Google Scholar
  (b) Hull, K. L.; Sanford, M. S. Catalytic and Highly Regioselective Cross-Coupling of Aromatic C − H Substrates. J. Am. Chem. Soc. 2007, 129, 11904. DOI: 10.1021/ja074395z.
   PubMed Web of Science ®Google Scholar
  (c) Seregin, I. V.; Ryabova, V.; Gevorgyan, V. Direct Palladium-Catalyzed Alkynylation of N-Fused Heterocycles. J. Am. Chem. Soc. 2007, 129, 7742. DOI: 10.1021/ja072718l.
   PubMed Web of Science ®Google Scholar
  (d) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C − H Bond Activation. Acc. Chem. Res. 2008, 41, 1013. DOI: 10.1021/ar800042p.
   PubMed Web of Science ®Google Scholar
  (e) Kakiuchi, F.; Murai, S. Catalytic C − H/Olefin Coupling. Acc. Chem. Res. 2002, 35, 826. DOI: 10.1021/ar960318p.
   PubMed Web of Science ®Google Scholar
  (f) Alberico, D.; Scott, M. E.; Lautens, M. Aryl − Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation. Chem. Rev. 2007, 107, 174. DOI: 10.1021/cr0509760.
   PubMed Web of Science ®Google Scholar
  (g) Roy, A. H.; Lenges, C. P.; Brookhart, M. Scope and Mechanism of the Intermolecular Addition of Aromatic Aldehydes to Olefins Catalyzed by Rh(I) Olefin Complexes. J. Am. Chem. Soc. 2007, 129, 2082. DOI: 10.1021/ja066509x.
   PubMed Web of Science ®Google Scholar
• Mikolos, N.; Aron, P.; Andrea, V.; Istvan, B.; Laszlo, T. Synthesis of benz[5,6]azepino[4,3-b]indoles by 1,7-electrocyclisation of azomethine ylides. Tetrahedron Lett. 2005, 46, 377. DOI: 10.1016/j.tetlet.2004.11.127.
   Google Scholar
• Niu, T.; Zhang, Y. Iron-Catalyzed Oxidative Homo-Coupling of Indoles via C–H Cleavage. Tetrahedron Lett. 2010, 51, 6847–6851. DOI: 10.1016/j.tetlet.2010.10.088.
   Web of Science ®Google Scholar
• Kim, I.; Choi, J. A Versatile Approach to Oligostilbenoid Natural Products – Synthesis of Permethylated Analogues of Viniferifuran, Malibatol A, and Shoreaphenol. Org. Biomol. Chem. 2009, 7, 2788. DOI: 10.1039/b901911a.
   PubMed Web of Science ®Google Scholar
• Zhang, W.; Sun, X.; Xia, P.; Huang, J.; Yu, G.; Wong, M. S.; Liu, Y.; Zhu, D. Novel Butterfly-Shaped Fused Heteroacenes: Synthesis, Properties, and Device Performance of Solution-Processed Field-Effect Transistors. Org. Lett. 2012, 14, 4382–4385. DOI: 10.1021/ol301852m.
   PubMed Web of Science ®Google Scholar
• Black, H. T.; Liu, S.; Sheares Ashby, V. Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors. Org. Lett. 2011, 13, 6492–6495. DOI: 10.1021/ol202662s.
   PubMed Web of Science ®Google Scholar
• Wirtanen, T.; Mäkelä, M. K.; Sarfraz, J.; Ihalainen, P.; Hietala, S.; Melchionna, M.; Helaja, J. Carbocatalysed Oxidative Csp2Csp2 Homocouplings of Benzo-Fused Heterocycles. Adv. Synth. Catal. 2015, 357, 3718–3726. DOI: 10.1002/adsc.201500664.
   Web of Science ®Google Scholar