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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 11
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Original Articles

Montmorillonite K10-catalyzed synthesis of N-fused imino-1,2,4-thiadiazolo isoquinoline derivatives

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Pages 1363-1376 | Received 08 Dec 2017, Published online: 02 Apr 2018

References

  • Frija, L. M. T.; Pombeiro, A. J. L.; Kopylovich, M. N. Building 1,2,4-Thiadiazole: Ten Years of Progress. Eur. J. Org. Chem. 2017, 2670–2682.
  • (a) Gaughan, E. Use of Substituted 1,2,4-Thiadiazoles for Killing Insects. U.S. Patent US 3755571 A, August 28, 1973. (b) Gay, W. A. Thiolcarbamate Derivatives of 3-Trihalomethyl-1,2,4-Thiadiazoles and Their Use as Herbicides. U.S. Patent US 4207089 A, June 10, 1980; (c) Katz, L. E. Selected 5-Hydrazono-3-Trichloromethyl-1,2,4-Thiadiazoles and Their Use as Foliar Fungicides. U.S. Patent US 4263312 A, April 21, 1981.
  • De, S.; Devasagayam, T. P. A.; Adhikari, S.; Menon, V. P. Antioxidant Properties of a Novel Marine Analogue of Dendrodoine. BARC Newsl. 2006, 273, 123–133.
  • (a) Castro, A.; Castano, T.; Encinas, A.; Porcal W.; Gil, C. Advances in the Synthesis and Recent Therapeutic Applications of 1,2,4-Thiadiazole Heterocycles. Bioorg. Med. Chem. 2006, 14, 1644–1652; (b) Iizawa, Y.; Okonogi, K.; Hayashi, R.; Iwahi, T.; Yamazaki, T.; Imada, A. Therapeutic Effect of Cefozopran (SCE-2787), a New Parenteral Cephalosporin, Against Experimental Infections in Mice. Antimicrob. Agents Chemother. 1993, 37, 100–105. DOI: 10.1016/j.bmc.2005.10.012.
  • Yang, Z.; Huang, N.; Xu, B.; Huang, W.; Xie, T.; Cheng, F.; Zou, K. Cytotoxic 1,3-Thiazole and 1,2,4-Thiadiazole Alkaloids from Penicillium oxalicum: Structural Elucidation and Total Synthesis. Molecules 2016, 21, 232. DOI: 10.3390/molecules21030232.
  • Porcal, W.; Hernandez, P.; Gonzalez, M.; Ferreira, A.; Olea-Azar, C.; Cerecetto, H.; Castro, A. Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties. J. Med. Chem. 2008, 51, 6150–6159. DOI: 10.1021/jm8006432.
  • Kumar, D.; Kumar, N. M.; Chang, K. H.; Gupta, R.; Shah, K. Synthesis and In-Vitro Anticancer Activity of 3,5-Bis(indolyl)-1,2,4-Thiadiazoles. Bioorg. Med. Chem. Lett. 2011, 21, 5897–5900. DOI: 10.1016/j.ejmech.2010.07.023.
  • (a) Unangst, P. C.; Shrum, G. P.; Connor, D. T.; Dyer, R. D.; Schrier, D. J. Novel 1,2,4-Oxadiazoles and 1,2,4-Thiadiazoles as Dual 5-Lipoxygenase and Cyclooxygenase Inhibitors. J. Med. Chem. 1992, 35, 3691–3698 (b) Kharimian, K.; Tam, T. F.; Leung-Toung, R. C. S. H.; Li, W. Thiadiazole Compounds Useful as Inhibitors of h+/k+ Atpase. PCT Int. Appl. WO9951584 A1, October 10, 1999.
  • Johnstone, C.; Mckerrecher, D.; Pike, K. G.; Waring, M. J. Hetroaryl Benzamide Derivatives for Use as Glk Activators in the Treatment of Diabetes. PCT Int. Appl. WO2005121110A1, December 22, 2005.
  • Craig, E. M.; George, A. B. Antimicrobial Bis(5-nitro-2-thiazolyl)thioisothiazoles and Thiadiazoles. U.S. Patent US 4209522, June 24, 1980.
  • Yamanaka, T.; Ohki, H.; Ohgaki, M.; Okuda, S.; Toda, A.; Kawabata, K.; Inoue, S.; Misumi, K.; Itoh, K.; Satoh, K. Cephem Compounds. U.S. Patent US 20050004094 A1, January 06, 2005.
  • Chakrabarti, J. K.; Smith, C. V.; Williamson, W. R. N. EU Pat. EP19910455356 A1, 1991.
  • Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cruz-Lopez, O.; Preti, D.; Tabrizi, M. A.; Fruttarolo, F.; Heilmann, F.; Bermejo, J.; Estevez, F. Hybrid Molecules Containing Benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazole and α-Bromoacryloyl Moieties as Potent Apoptosis Inducers on Human Myeloid Leukaemia Cells. Bioorg. Med. Chem. Lett. 2007, 17, 2844–2848. DOI: 10.1016/j.bmcl.2007.02.048.
  • Leung-Toung, R.; Wodzinska, J.; Li, W.; Lowrie, J.; Kukreja, R.; Desilets, D.; Karimian, K.; Tam, T. F. 1,2,4-Thiadiazole: A Novel Cathepsin B Inhibitor. Bioorg. Med. Chem. 2003, 11, 5529–5537.
  • Yoshimura, A.; Todora, A. D.; Kastern, B. J.; Koski, S. R.; Zhdankin, V. V. Synthesis of 1,2,4-Thiadiazoles by Oxidative Dimerization of Carbothioamides by Using Oxone. Eur. J. Org. Chem. 2014, 2014, 5149–5152. DOI: 10.1002/ejoc.201402756.
  • Kushwaha, N.; Kushwaha, S. K. S.; Rai, A. K. Biological Activities of Thiadiazole Derivatives: A Review. Int. J. Chem. Tech. Res. 2012, 4, 517–531.
  • (a) Mariappan, A.; Rajaguru, K.; Chola, N. M.; Muthusubramanian, S.; Bhuvanesh, N. Hypervalent Iodine(III) Mediated Synthesis of 3-Substituted 5-Amino-1,2,4-thiadiazoles Through Intramolecular Oxidative S‒N Bond Formation. J. Org. Chem. 2016, 81, 6573–6579; (b) Wang, B.; Meng, Y.; Zhou, Y.; Ren, L.; Wu, J.; Yu, W.; Chang, J. Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I2-Mediated Oxidative N‒S Bond Formation. J. Org. Chem. 2017, 82, 5898–5903 (c) Ruel, R.; L’Heureux, A.; Thibeault, C.; Daris, J. P.; Martel, A.; Price, L. A.; Wu, Q.; Hua, J.; Wexler, R. R.; Rehfuss, R.; Lam, P. Y. S. New Azole Antagonists with High Affinity for the P2Y1 Receptor. Bioorg. Med. Chem. Lett. 2013, 23, 3519–3522. DOI: 10.1016/j.bmcl.2013.04.041.
  • Xie, H.; Cai, J.; Wang, Z.; Huang, H.; Deng, G. J. A Three-Component Approach to 3,5-Diaryl-1,2,4-thiadiazoles Under Transition-Metal-Free Conditions. Org. Lett. 2016, 18, 2196–2199. DOI: 10.1002/chin.201637114.
  • Tumula, N.; Jatangi, N.; Palakodety, R. K.; Balasubramanian, S.; Nakka, M. I2-Catalyzed Oxidative N−S Bond Formation: Metal-Free Regiospecific Synthesis of N-Fused and 3,4-Disubstituted 5-Imino1,2,4-thiadiazoles. J. Org. Chem. 2017, 82, 5310–5316.
  • Rocchi, D.; González, J. F.; Menendez, J. C. Montmorillonite Clay-Promoted, Solvent-Free Cross-Aldol Condensations Under Focused Microwave Irradiation. Molecules 2014, 19, 7317–7326. DOI: 10.3390/molecules19067317.
  • Kaur, N.; Kishore, D. Montmorillonite: An Efficient, Heterogeneous and Green Catalyst for Organic Synthesis. J. Chem. Pharm. Res. 2012, 4, 991–1015.
  • Dintzner, M. R.; Morse, K. M.; McClelland, K. M.; Coligado, D. M. Investigation of the Montmorillonite Clay-Catalyzed [1,3] Shift Reaction of 3-Methyl-2-Butenyl Phenyl Ether. Tetrahedron Lett. 2004, 45, 79–81. DOI: 10.1016/j.tetlet.2003.10.119.
  • (a) Nagendrappa, G. Organic Synthesis Using Clay and Clay Supported Catalysts. Appl. Clay Sci. 2011, 53, 106–138; (b) Loh, T. P.; Li, X. R. Clay Montmorillonite KI0 Catalyzed Aldol-Type Reaction of Aldehydes with Silyl Enol Ethers in Water. Tetrahedron 1999, 55, 10789–10802.
  • (a) Lambat, T. L.; Deo, S. S.; Inam, F. S.; Deshmukh, T. B.; Bhat, A. R. Montmorillonite K10: An Efficient Organo Heterogeneous Catalyst for One-Pot Synthesis of New N,N′-Alkylidene Bisamide Derivatives Under Solvent Free Condition. Karbala Int. J. Modern Sci. 2016, 2, 63–68; (b) Sharma, G. V. R.; Devi, B.; Reddy, K. S.; Reddy, M. V.; Kondapi, A. K.; Bhaskar, C. Montmorillonite K10 Catalyzed Multi Component Reactions (MCR): Synthesis of Novel Thiazolidinones as Anticancer Agents. Heterocycl. Commun. 2015, 21, 187–190; (c) Sharma, G. V. R.; Devi, B.; Naidu, A. A.; Robert, A. R. One Pot Multi Component Reaction (MCR) Catalysed by Montmorillonite K10 Under Microwave Conditions: Synthesis of Novel 1-(2,7-Dimethyl-5-phenyl-5H-thiazolo[3,2-a]pyrimidin-6-yl)ethanone Derivatives. Curr. Microwave Chem. 2016, 3, 200–202. DOI: 10.2174/2213335602666151012193348.
  • (a) Bharate, J. B.; Sharma, R.; Aravinda, S.; Gupta, V. K.; Singh, B.; Bharate, S. B.; Vishwakarma, R. A. Montmorillonite Clay Catalyzed Synthesis of Functionalized Pyrroles Through Domino Four-Component Coupling of Amines, Aldehydes, 1,3-Dicarbonyl Compounds and Nitroalkanes. RSC Adv. 2013, 3, 21736–21742; (b) Kumaran, E.; Santhi, M.; Balasubramanian, K. K.; Bhagavathy, S. Montmorillonite K-10 Clay-Catalyzed Ferrier Rearrangement of 2-C-Hydroxymethyl-d-Glycals, 3,4,6-Tri-O-alkyl-d-glycals, and 3,4-(Dihydro-2H-pyran-5-yl)methanol: A Few Unexpected Domino Transformations. Carbohydr. Res. 2011, 346, 1654–1661. DOI: 10.1039/c3ra43324b.
  • Kumar, B. S.; Dhakshinamoorthy, A.; Pitchumani, K. K10 Montmorillonite Clays as Environmentally Benign Catalysts for Organic Reactions. Catal. Sci. Technol. 2014, 4, 2378–2396. DOI: 10.1039/c4cy00112e.
  • Chacko, P.; Shivashankar, K. Nano Structured Spinel Co3O4-Catalyzed Four Component Reaction: A Novel Synthesis of Ugi Adducts from Aryl Alcohols as a Key Reagent. Chin. Chem. Lett. 2017, 28, 1619–1624. DOI: 10.1016/j.cclet.2017.04.015.
  • Chacko, P.; Shivashankar, K. I2-catalyzed One-Pot Synthesis of Benzofuro/Thieno[2,3-b]Pyrrole Motifs. Tetrahedron 2018, 74, 1520–1526.
  • Nadaf, A. N.; Shivashankar, K. CFL Light-Promoted One-Pot Synthesis of Pyrano[3,2-c] 5 Chromen-5(4H)-Ones. Synth. Commun. 2018, 48, 809–815.
  • Beerappa, M.; Shivashankar, K. Four Component Synthesis of Highly Functionalized Pyrano[2,3-c]Pyrazoles from Benzyl Halides. Synth. Commun. 2018, 48, 146–154. DOI: 10.1080/00397911.2017.1386788.
  • Beerappa, M.; Shivashankar, K. Multicomponent Reaction of Benzyl Halides: Synthesis of [1,2,4]Triazolo/Benzimidazolo Quinazolinones. Synth. Commun. 2016, 46, 421–432. DOI: 10.1080/00397911.2016.1140784.
  • Shamala, D.; Shivashankar, K.; Chandra; Mahendra, M. Synthesis of N1 and N2 Coumarin Substituted 1,2,3-Triazole Isomers Via Click Chemistry Approach. Synth. Commun. 2016, 46, 433–441. DOI: 10.1080/00397911.2016.1140785.
  • Shamala, D.; Shivashankar, K. Synthesis of Pyridazinones via Molecular-Iodine-Mediated Cleavage of 4-Bromomethylcoumarin Precursors. Synth. Commun. 2016, 46, 1735–1740. DOI: 10.1080/00397911.2016.1223310.
  • Shamala, D.; Shivashankar, K. Synthesis of 4-Phenyloxazinones via DBU-Catalyzed Cleavage of 4-Bromomethylcoumarins. Synth. Commun. 2017, 47, 105–110. DOI: 10.1080/00397911.2016.1252045.
  • Jagadishbabu, N.; Shivashankar, K. Biginelli Reaction of Vicinal Diols: A New Route for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-One Derivatives. Lett. Org. Chem. 2017, 14, 330–336. DOI: 10.2174/1570178614666170310123511.
  • Neumeyer, J. L.; Weinhardt, K. K. Isoquinolines. 1. 3-Amino- and 3-Fluoroisoquinoline Derivatives as Potential Antimalarials. J. Med. Chem. 1970, 13, 613–616.
  • Darin, D. V.; Selivanov, S. I.; Lobanov, P. S.; Potekhin, A. A. Cyclocondensation of 2-Fluoro-5-nitrobenzaldehyde with Amidines. New Synthesis of Isoquinolines. Chem. Heterocycl. Compd. 2004, 40, 888–894.

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