Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 22
143
Views
7
CrossRef citations to date
0
Altmetric
Articles

Green and complementary regioselective synthesis of 3-(1 –substituted pyrazol-3(or 5)-yl)indoles from β-ethyltho-β-indolyl-α,β-unsaturated ketones in water

, , &
Pages 3404-3412 | Received 05 Jun 2020, Published online: 03 Aug 2020

Reference

  • (a) Sechi, M.; Innocenti, A.; Pala, N.; Rogolino, D.; Carcelli, M.; Scozzafava, A.; Supuran, C. T. Inhibition of α-Class Cytosolic Human Carbonic Anhydrases I, II, IX and XII, and β-Class Fungal Enzymes by Carboxylic Acids and Their Derivatives: New isoform-I Selective Nanomolar Inhibitors. Bioorg. Med. Chem. Lett. 2012, 22, 5801–5806. DOI: 10.1016/j.bmcl.2012.07.094. (b) Esvan, Y. J.; Giraud, F.; Pereira, E.; Suchaud, V.; Nauton, L.; Théry, V.; Dezhenkova, L. G.; Kaluzhny, D. N.; Mazov, V. N.; Shtil, A. A.; et al. Synthesis and Biological Activity of Pyrazole Analogues of the Staurosporine Aglycon K252c. Bioorg. Med. Chem. 2016, 24, 3116–3124. DOI: 10.1016/j.bmc.2016.05.032. (c) Cadoni, R.; Pala, N.; Lomelino, C.; Mahon, B. P.; McKenna, R.; Dallocchio, R.; Dessì, A.; Carcelli, M.; Rogolino, D.; Sanna, V.; et al. Exploring Heteroaryl-Pyrazole Carboxylic Acids as Human Carbonic Anhydrase XII Inhibitors. ACS Med Chem Lett. 2017, 8, 941–946. DOI: 10.1021/acsmedchemlett.7b00229.
  • Rao, D. S.; Rao, A. A.; Reddy, S. Letters. Der PharmaChemica. 2000, 3, 301–309. DOI: 10.1016/S1094-6950(06)60127-3.
  • Somappa, S. B.; Biradar, J. S.; Rajesab, P.; Rahber, S.; Sundar, M. A One-Pot Synthesis of Indole-Appended Heterocycles as Potent anti-Inflammatory, Analgesic, and CNS Depressant Agents. Monatsh. Chem. 2015, 146, 2067–2078. DOI: 10.1007/s00706-015-1476-x.
  • (a) El-Mekabaty, A.; Etman, H. A.; Mosbah, A. Synthesis of Some New Fused Pyrazole Derivatives Bearing Indole Moiety as Antioxidant Agents. J. Heterocyclic Chem. 2016, 53, 894–900. DOI: 10.1002/jhet.2218. (b) Ummadi, N.; Gundala, S.; Venkatapuram, P.; Adivireddy, P. Synthesis and Antioxidant Activity of a New Class of Pyrazolyl Indoles, Thiazolyl Pyrazolyl Indoles. Med. Chem. Res. 2017, 26, 1574–1584. DOI: 10.1007/s00044-017-1827-8.
  • (a) Kumar, S. V.; Yadav, S. K.; Raghava, B.; Saraiah, B.; Ila, H.; Rangappa, K. S.; Hazra, A. Cyclocondensation of Arylhydrazines with 1,3-Bis(Het)Arylmonothio-1,3-Diketones and 1,3-Bis(Het)Aryl-3-(Methylthio)-2-Propenones: Synthesis of 1-Aryl-3,5-Bis(Het)Arylpyrazoles with Complementary Regioselectivity. J. Org. Chem. 2013, 78, 4960–4973. − DOI: 10.1021/jo400599e. (b) Gupton, J. T.; Telang, N.; Gazzo, D. F.; Barelli, P. J.; Lescalleet, K. E.; Fagan, J. W.; Mills, B. J.; Finzel, K. L.; Kanters, R. P. F.; Crocker, K. R.; et al. Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles. Tetrahedron. 2013, 69, 5829–5840. DOI: 10.1016/j.tet.2013.05.045. (c) Usachev, B. I.; Obydennov, D. I.; Kodess, M. I.; Sosnovskikh, V. Y. Regioselective Solvent-Sensitive Reactions of 6-(Trifluoromethyl)Comanic Acid and Its Derivatives with Phenylhydrazine. Tetrahedron Lett. 2009, 50, 4446–4448. DOI: 10.1016/j.tetlet.2009.05.056.
  • (a) Kumari, S.; Shekhar, A.; Pathak, D. D. Graphene Oxide–TiO 2 Composite: An Efficient Heterogeneous Catalyst for the Green Synthesis of Pyrazoles and Pyridines. New J. Chem. 2016, 40, 5053–5060. DOI: 10.1039/C5NJ03380B. (b) Hazra, S.; Deb, M.; Elias, A. Iodine Catalyzed Oxidation of Alcohols and Aldehydes to Carboxylic Acids in Water: A Metal-Free Route to the Synthesis of Furandicarboxylic Acid and Terephthalic Acid. Green Chem. 2017, 19, 5548–5552. DOI: 10.1039/C7GC02802D. (c) Wu, C.; Lu, L. H.; Peng, A. Z.; Jia, G. K.; Peng, C.; Cao, Z.; Tang, Z.; He, W. M.; Xu, X. Ultrasound-Promoted Brønsted Acid Ionic Liquid-Catalyzed Hydrothiocyanation of Activated Alkynes under Minimal Solvent Conditions. Green Chem. 2018, 20, 3683–3688. DOI: 10.1039/C8GC00491A. (d) Pakamorė, I.; Rousseau, J.; Rousseau, C.; Monflier, E.; Szilágyi, P. Á. An Ambient-Temperature Aqueous Synthesis of Zirconium-Based Metal–Organic Frameworks. Green Chem. 2018, 20, 5292–5298. DOI: 10.1039/C8GC02312C. (e) Xie, L. Y.; Peng, S.; Liu, F.; Liu, Y. F.; Sun, M.; Tang, Z. L.; Jiang, S.; Cao, Z.; He, W. M. Clean Preparation of Quinolin-2-yl Substituted Ureas in Water. ACS Sustainable Chem. Eng. 2019, 7, 7193–7199. DOI: 10.1021/acssuschemeng.9b00200. (f) Zhang, Q.; Q.; Ge, Y. C.; Yang, C. J.; Zhang, B. G.; Deng Enhanced Photocatalytic Performance for Oxidation of Glucose to Value-Added Organic Acids in Water Using Iron Thioporphyrazine Modified SnO2. Green Chem. 2019, 21, 5019–5029. DOI: 10.1039/C9GC01647C.
  • Dong, D. W.; Ouyang, Y.; Yu, H. F.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. Chemoselective Thioacetalization in Water: 3-(1,3-Dithian-2-Ylidene)Pentane-2,4-Dione as an Odorless, Efficient, and Practical Thioacetalization Reagent. J. Org. Chem. 2005, 70, 4535–4537. DOI: 10.1021/jo050271y.
  • Yu, H. F.; Liao, P. Q. DBSA-Catalyzed Friedel–Crafts Alkylation of Cyclic Ketene Dithioacetals with Alcohols in Water. Tetrahedron Lett. 2016, 57, 2868–2872. DOI: 10.1016/j.tetlet.2016.05.062.
  • 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: 10.1080/00397911.2017.1368084.
  • (a) Yu, H. F.; Yu, Z. K. Direct Alkenylation of Indoles with Alpha-Oxo Ketene Dithioacetals: Efficient Synthesis of Indole Alkaloids Meridianin Derivatives. Angew. Chem. Int. Ed. Engl. 2009, 48, 2929–2933. DOI: 10.1002/anie.200900278. (b) Wang, W. J.; Yu, H. F. Feasible Selective Synthesis of 3-Acetylindoles and 3-Acetoacetylindoles from β-Ethylthio-β-Indoly α, β-Unsaturated Ketones. Synth. Commun. 2019, 49, 377–385. DOI: 10.1080/00397911.2018.1555851. (c) Hu, X. Y.; Yu, H. F.; Wang, W. J.; Jiang, S. A.; Liu, Q.; He, J. Synthesis of 3-Ethanoyl/Aroylacetylindoles in Water. Chin. J. Org. Chem. 2019, 39, 3183–3189. DOI: 10.6023/cjoc201904002.
  • Yu, H. F.; Wang, W. Catalyst Free Cyclocondensation of β-Ethylthio-β-Indolyl-α, β-Unsaturated Ketones with Hydrazines: Efficient Synthesis of 3-Pyrazolyl Indoles. J. Synth. Commun. 2020, 50, 1133–1140. DOI: 10.1080/00397911.2019.1681001.
  • Zhao, Y. H.; Yu, H. F.; Liao, P. Q.; Wang, W. J. Chem. Res. Chin. Univ. 2020. DOI: 10.1007/s40242-019-0011-8.
  • Yu, H. F.; Liao, P. Q.; Mei, Z. M. Regioselective Synthesis of Isomeric 3-[1-Substituted Pyrazol-3(5)-yl]Indoles from β-Ethylthio-β-Indolyl-α,β-Unsaturated Ketones. Synthesis. 2020, 52, 2111–2120. DOI: 10.1055/s-0040-1707999.
  • (a) Yu, H. F.; Li, T. C.; Liao, P. Q. Iron(III) Chloride Promoted Desulfitative C–C Coupling Reaction of α-Oxo Ketene Dithioacetals and Indoles: Highly Selective Synthesis of β,β-Bisindolyl and β-Indolyl α,β-Unsaturated Carbonyl Compounds. Synthesis. 2012, 44, 3743–3756. DOI: 10.1055/s-0032-1317691. (b) 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. DOI: 10.6023/cjoc201403055. (c) Yu, H. F.; Li, T. C.; Liao, P. Q.; Diao, Q. P.; Xin, G.; Hou, D. Acidity-Controlled Indolylation of 3, 3-Bis(Ethylthio)Acrylate. Chin. J. Org. Chem. 2014, 34, 956–961. DOI: 10.6023/cjoc201312020.
  • (a) Dieter, R. K. α-Oxo Ketene Dithioacetals and Related Compounds: Versatile Three-Carbon Synthons. Tetrahedron. 1986, 42, 3029–3096. DOI: 10.1016/S0040-4020(01)87376-2. (b) Junjappa, H.; Ila, H.; Asokan, C. V. α-Oxoketene-S,S-, N,S- and N,N-Acetals: Versatile Intermediates in Organic Synthesis. Tetrahedron. 1990, 46, 5423–5506. DOI: 10.1016/S0040-4020(01)87748-6. (c) Pan, L.; Liu, Q. [5 + 1]-Annulation Strategy Based on Alkenoyl Ketene Dithioacetals and Analogues. Synlett. 2011, 2011, 1073–1080. DOI: 10.1055/s-0030-1260540. (d) Pan, L.; Bi, X. H.; Liu, Q. Recent Developments of Ketene Dithioacetal Chemistry. Chem. Soc. Rev. 2013, 42, 1251–1286. DOI: 10.1039/c2cs35329f. (e) Yu, H.; Jin, W.; Sun, C.; Chen, J.; Du, W.; He, S.; Yu, Z. Palladium-Catalyzed Cross-Coupling of Internal Alkenes with Terminal Alkenes to Functionalized 1,3-Butadienes Using C-H Bond Activation: Efficient Synthesis of Bicyclic Pyridones. Angew. Chem. Int. Ed. Engl. 2010, 49, 5792–5797. DOI: 10.1002/anie.201002737. (f) 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. DOI: 10.1055/s-0036-1588982. (g) Zhao, H.; Diao, Q. P.; Yu, H. F.; Li, T. C.; Liao, P. Q.; Hou, D. Y. FeCl3·6H2O-Catalyzed Synthesis of β-Ketothioesters from Chain α-Oxo Ketene Dithioactals. Chem. Res. Chin. Univ. 2017, 33, 746–752. DOI: 10.1007/s40242-017-7082-1.

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.