Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 3
255
Views
10
CrossRef citations to date
0
Altmetric
Articles

Feasible selective synthesis of 3-Acetylindoles and 3-Acetoacetylindoles from β-ethylthio-β-indoly α, β-unsaturated ketones

&
Pages 377-385 | Received 10 Nov 2018, Published online: 29 Jan 2019

References

  • (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chem. Rev. 2003, 103, 893-930. (b) Humphrey, G. R.; Kuethe, J. T. Practical Methodologies for the Synthesis of Indoles. Chem. Rev. 2006, 106, 2875-2911. (c) Vasiljevik, T.; Franks, L. N.; Ford, B. M.; Douglas, J. T.; Prather, P. L.; Fantegrossi, W. E.; Prisinzano, T. E. Design, Synthesis, and Biological Evaluation of Aminoalkylindole Derivatives as Cannabinoid Receptor Ligands with Potential for Treatment of Alcohol Abuse. J. Med. Chem. 2013, 56, 4537-4550. (d) Li, Y.; Zhu, S.; Li, J.; Li, A. Asymmetric Total Syntheses of Aspidodasycarpine, Lonicerine, and the Proposed Structure of Lanciferine. J. Am. Chem. Soc. 2016, 138, 3982-3985. doi:10.1021/cr020033s
  • (a) Robinson, B. Reduction of Indoles and Related Compounds. Chem. Rev. 1969, 69, 785-797. (b) Wu, Y. S.; Coumar, M. S.; Chang, J. Y.; Sun, H. Y.; Kuo, F. M.; Kuo, C. C.; Chen, Y. J.; Chang, C. Y.; Hsiao, C. L.; Liou, J. P.; et al. Synthesis and Evaluation of 3-Aroylindoles as Anticancer Agents: Metabolite Approach. J. Med. Chem. 2009, 52, 4941-4945. (c) Carbone, A.; Spanò, V.; Parrino, B.; Ciancimino, C.; Attanasi, O.; Favi, G. A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin. Molecules. 2013, 18, 2518-2527. (d) Sechi, M.; Derudas, M.; Dallo-Cchio, R.; Dessı`, A.; Bacchi, A.; Sannia, L.; Carta, F.; Palomba, M.; Ragab, O.; Chan, C.; et al. Design and Synthesis of Novel Indole β-Diketo Acid Derivatives as HIV-1 Integrase Inhibitors. J. Med. Chem. 2004, 47, 5298-5310. doi:10.1021/cr60262a003
  • (a) Taylor, J. E.; Jones, M. D.; Williams, J. M. J.; Bull, S. D. Friedel − Crafts Acylation of Pyrroles and Indoles Using 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) as a Nucleophilic Catalyst. Org. Lett. 2010, 12, 5740-5743. (b) Guchhait, S. K.; Kashyap, M.; Kamble, H. ZrCl 4 -Mediated Regio- and Chemoselective Friedel-Crafts Acylation of Indole. J. Org. Chem. 2011, 76, 4753-4758. (c) Zhang, L.; Yi, F.; Zou, J.; Qu, S. Iron Powder Promoted Regio-Selective Friedel-Crafts Acylation of Indole under Solvent-Free Conditions. Asian. J. Chem. 2013, 25, 6117-6120. (d) Shi, Q.; Li, P.; Zhu, X.; Wang, L. Decarboxylative/Decarbonylative C3-Acylation of Indoles via Photocatalysis: A Simple and Efficient Route to 3-Acylindoles. Green Chem. 2016, 18, 4916-4923. doi:10.1021/ol1025348
  • (a) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970. (b) Allen, M. S.; Hamaker, L. K.; La Loggia, A. J.; Cook, J. M. Entry into 6-Methoxy-D(+)-Tryptophans. Stereospecific Synthesis of 1-Benzenesulfonyl-6-methoxy-D(+)-Tryptophan Ethyl Ester. Synth. Commun. 1992, 22, 2077-2102.
  • (a) Macor, J. E.; Blank, D. H.; Fox, C. B.; Lebel, L. A.; Newman, M. E.; Post, R. J.; Ryan, K.; Schmidt, A. W.; Schulz, D. W.; Koe, B. K. 5-[(3-Nitropyrid-2-yl)amino]indoles: Novel Serotonin Agonists with Selectivity for the 5-HT1D Receptor. Variation of the C3 Substituent on the Indole Template Leads to Increased 5-HT1D Receptor Selectivity. J. Med. Chem. 1994, 37, 2509-2512. (b) Davidsen, S. K.; Summers, J. B.; Albert, D. H.; Holms, J. H.; Heyman, H. R.; Magoc, T. J.; Conway, R. G.; Rhein, D. A.; Carter, G. W. J. N-(Acyloxyalkyl)Pyridinium Salts as Soluble Prodrugs of a Potent Platelet Activating Factor Antagonist. J. Med. Chem. 1994, 37, 4423-4429. (c) Zhang, Z. W.; Xue, H.; Li, H. L.; Kang, H. P.; Feng, J.; Lin, A.; J.; Liu, S. X. Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)Indoles from Free (N-H) Indoles via Common N -Indolyl Triethylborate. Org. Lett. 2016, 18, 3918-3921. doi:10.1021/jm00042a003
  • Bergman, J.; Backvall, J. E.; Lindstrom, J. O. Synthesis and Reactions of Some 3-(2-haloacyl)Indoles. Tetrahedron. 1973, 29, 971-976. doi:10.1016/0040-4020(73)80047-X
  • (a) Jiang, T. S.; Wang, G.; W. Synthesis of 3-Acylindoles by Palladium-Catalyzed Acylation of Free(N-H) Indoles with Nitriles. Org. Lett. 2013, 15, 788-791. (b) Giles, R. G.; Heaney, H.; Plater, M. J. Reactions of Nitrilium Salts with Indole and Pyrrole and Their Derivatives in the Synthesis of Imines, ketones and Secondary Amines. Tetrahedron 2015, 71, 7367-7385. DOI: doi:10.1016/j.tet.2015.05.005
  • Wu, W.; Su, W. Mild and Selective Ru-catalyzed Formylation and Fe-catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source. J. Am. Chem. Soc. 2011, 133, 11924-11927. doi:10.1021/ja2048495
  • (a) Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Palladium-Catalyzed Oxidative Cyclization of N -Aryl Enamines: From Anilines to Indoles. Angew. Chem., Int. Ed. 2008, 47, 7230-7233. b) Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N -Aryl Enaminones. Angew. Chem., Int. Ed. 2009, 48, 8078-8081. (c) Guan, Z. H.; Yan, Z. Y.; Ren, Z. H.; Liu, X. Y.; Liang, Y. M. Preparation of Indoles via Iron Catalyzed Direct Oxidative Coupling. Chem. Commun. 2010, 46, 2823-2825. (d) Neumann, J. J.; Rakshit, S.; Dröge, T.; Würtz, S.; Glorius, F. Exploring the Oxidative Cyclization of Substituted N-Aryl Enamines: Pd-Catalyzed Formation of Indoles from Anilines. Chem. Eur. J. 2011, 17, 7298-7303. (e) Huang, F.; Wu, P.; Wang, L. D.; Chen, J. P.; Sun, C. L.; Yu, Z. K. Copper-Mediated Intramolecular Oxidative C-H/C-H Cross-Coupling of α-Oxo Ketene N,S-Acetals for Indole Synthesis. J. Org. Chem. 2014, 79, 10553-10560. doi:10.1002/anie.200802482
  • Vedran, H. J. Heterocycl. Chem 2007, 44, 1213-1217.
  • Kostryukova, T. S.; Ivanovskaya, N. P.; Lyamin, A. I.; Romanov, D. V.; Osin, N. S.; Zatonsky, G. V.; Vasil’ev, N. V. Synthesis and Luminescence-spectral Properties of Benzoheterocyclic β-Diketones and Their Complexes with Europium. Russ. J. Gen. Chem. 2012, 82, 455-460. DOI: doi:10.1134/S1070363212030152.
  • Jan, B. A. Acta Chem. Scandinavica. 1968, 22, 1063-1066.
  • (a) Yu, H. F.; Yu, Z. K. Direct Alkenylation of Indoles with α-Oxo Ketene Dithioacetals: Efficient Synthesis of Indole Alkaloids Meridianin Derivatives. Angew. Chem. Int. Ed. 2009, 48, 2929-2933. (b)Yu, H.; Li, T.; Liao, P. 3743-3756.. (c) Yu, H. F.; Liao, P. Q.; Diao, Q. P.; Li, T. C.; Xin, G.; Han, L. N.; Hou, D. Y. Selective Synthesis of 3-(3-Indolyl)-3-(Methylthio)Acrylate and 3-(3-Indolyl)-3-Oxopropanoate. Chin. J. Org. Chem. 2014, 34, 1851-1856. (d) Yu, H. F.; Li, T. C.; Liao, P. Q.; Diao, Q. P.; Xin, G.; Hou, D. Y. Acidity-Controlled Indolylation of 3, 3-Bis(ethylthio)Acrylate. Chin. J. Org. Chem. 2014, 34, 956-961. (e) Zhao, H.; Zhang, F. W.; Yu, H. F.; Liao, P. Q.; Diao, Q. P.; Li, T. C.; Xin, G.; Hou, D. Y. FeCl 3 -Catalyzed Friedel-Crafts Alkylation of α -Hydroxy Ketene Dithioacetals with Indoles. Chin. J. Org. Chem. 2015, 35, 1493-1499. doi:10.1002/anie.200900278
  • (a) Yu, H. F.; Zhao, L. J.; Diao, Q.; P.; Li, T. C.; Liao, P. Q.; Hou, D. Y.; Xin, G.; FeCl3·6H2O-Catalyzed Tandem Alkylation-Hydrolysis Reaction of Chain α-Oxo Ketene Dithioacetals with Alcohols: Efficient Synthesis of α-Alkylated β-Oxo Thioesters. Synlett. 2017, 28, 1828-1834. (b) Zhao, H.; Diao, Q.; Yu, H.; Li, T.; Liao, P.; Hou, D. FeCl3·6H2O-catalyzed Synthesis of β-Ketothioesters from Chain α-Oxo Ketene Dithioactals. Chem. Res. Chin. Univ. 2017, 33, 746-752. (c) Qi, F.; Yu, H. F.; Wang, Y. N.; Lv, Y.; Li, Y. X.; Han, L.; Wang, R.; Feng, X. N. DBSA-catalyzed Hydrolysis of Chain α -Oxo Ketene Dithioacetals in Water: Aqueous Synthesis of β -Ketothioesters. Synth. Commun. 2017, 47, 2220-2224. doi:10.1055/s-0036-1588982
  • (a) Okauchi, T.; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino, H. A General Method for Acylation of Indoles at the 3-Position with Acyl Chlorides in the Presence of Dialkylaluminum Chloride. Org. Lett. 2000, 2, 1485-1487. (b) Borah, A. J.; Shi, Z. Z. Palladium-Catalyzed Regioselective C-H Fluoroalkylation of Indoles at the C4-Position. Chem. Commun. 2017, 53, 3945-3948. DOI: doi:10.1021/ol005841p.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.