Easy installation of 1,2,3-triazoles or iodo-1,2,3-triazoles onto indole-fused oxazinones via CuAAC-based MCR in the presence of 18-crown-6

References

• (a) Verpoorte, R. Antimicrobially Active Alkaloids. In Alkaloids: Biochemistry, Ecology And Medicinal Applications, Roberts, M. R., Wink, M., Eds.; Plenum Press: New York, 1998; pp 397–433.
   Google Scholar
  (b) McKay, M. J.; Carroll, A. R.; Quinn, R. J.; Hooper, J. N. A. 1,2-Bis(1H-Indol-3-yl)Ethane-1,2-Dione, an Indole Alkaloid from the Marine Sponge Smenospongia sp. J. Nat. Prod. 2002, 65, 595–597. DOI: 10.1021/np010347v.
   PubMed Web of Science ®Google Scholar
• Kleinwachter, P.; Schlegel, B.; Groth, I.; Hartl, A.; Grafe, U. New Inhibitors of 3α-Hydroxysteroid Dehydrogenase, 0231A and 0231B from Streptomyces sp. HKI 0231. J. Antibiot. 2001, 54, 510–512. DOI: 10.7164/antibiotics.54.510.
   PubMed Web of Science ®Google Scholar
• Fernández-Pérez, F.; Almagro, L.; Pedreño, M. A.; Gómez Ros, L. V. Synergistic and Cytotoxic Action of Indole Alkaloids Produced from Elicited Cell Cultures of Catharanthusroseus. Pharm. Biol 2013, 51, 304–310. DOI: 10.3109/13880209.2012.722646.
   PubMed Web of Science ®Google Scholar
• Kaushik, N. K.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C. H.; Verma, A. K.; Choi, E. H. Biomedical Importance of Indoles. Molecules 2013, 18, 6620–6662. DOI: 10.3390/molecules18066620.
   PubMed Web of Science ®Google Scholar
• Rajan, S.; Puri, S.; Kumar, D.; Babu, M. H.; Shankar, K.; Varshney, S.; Srivastava, A.; Gupta, A.; Reddy, M. S.; Gaikad, A. N. Novel Indole and Triazole Based Hybrid Molecules Exhibit Potent anti-Adipogenic and Antidyslipidemic Activity by Activating Wnt3a/β-Catenin Pathway. Eur. J. Med. Chem. 2018, 143, 1345–1360. DOI: 10.1016/j.ejmech.2017.10.034.
   PubMed Web of Science ®Google Scholar
• Minvielle, M. J.; Bunders, C. A.; Melander, C. Indole–Triazoleconjugates are Selective Inhibitors and Inducers of Bacterial Biofilms. Med. Chem. Commun. 2013, 4, 916–919. DOI: 10.1039/c3md00064h.
   Web of Science ®Google Scholar
• Pawar, K.; Yadav, A.; Prasher, P.; Mishra, S.; Singh, B.; Singh, P.; Komath, S. S. Identification of an Indole–Triazole–Amino Acid Conjugate as a Highly Effective Antifungal Agent. Med. Chem. Commun. 2015, 6, 1352–1359. DOI: 10.1039/C5MD00156K.
   Web of Science ®Google Scholar
• Reddy, B. S.; Reddy, B. S.; Rao, C.; Subha, M. C. S. Synthesis of Some New 1,2,3-Triazole Derivatives of Indole with Potential Antimicrobial Activity. World J. Pharm. Pharm. Sci. 2015, 4, 1084–1090.
   Google Scholar
• Naveen, P.; Nikhila, G.; Udayakumar, D.; Pulla, V. K.; Perumal, Y.; Dharmarajan, S. Synthesis of Novel 5-[(1,2,3-Triazol-4-yl)Methyl]1-1methyl-3Hpyridazino[4,5-b]Indol-4-One by Click Reaction and Exploration Anticancer Activity. Med. Chem. Res. 2016, 25, 135–148. DOI: 10.1007/s00044-015-1473-y.
   Web of Science ®Google Scholar
• D’Ambra, T. E.; Estep, K. G.; Bell, M. R.; Eissenstat, M. A.; Josef, K. A.; Ward, S. J.; Haycock, D. A.; Baizman, E. R.; Casiano, F. M.; Beglin, N. C.; et al. Conformationally Restrained Analogs of Pravadoline: Nanomolar Potent, Enantioselective, (Aminoalkyl)Indole Agonists of the Cannabinoid Receptor. J. Med. Chem. 1992, 35, 124–135. DOI: 10.1021/jm00079a016.
   PubMed Web of Science ®Google Scholar
• Ayral-Kaloustian, S.; Zhang, N.; Venkatesan, A. M.; Mansour, T. S.; Nguyen, T. H.; Anderson, J. T. [a]​-​Fused indole compounds, their use as mTOR kinase and PI3 kinase inhibitors for treating cancer, and their syntheses. US 20090192147 A1 20090730. U.S. Pat. Appl. Publ. 2009.
   Google Scholar
• (a) Radwan, M. A. A.; Ragab, E. A.; Sabry, N. M.; El-Shenawy, S. M. Synthesis and Biological Evaluation of New 3-Substituted Indole Derivatives as Potential anti-Inflammatory and Analgesic Agents. Bioorg. Med. Chem 2007, 15, 3832–3841. DOI: 10.1016/j.bmc.2007.03.024.
   PubMed Web of Science ®Google Scholar
  (b) Sharma, V.; Kumar, P.; Pathak, D. Biological Importance of the Indole Nucleus in Recent Years: A Comprehensive Review. J. Heterocycl. Chem. 2010, 47, 491–502. DOI: 10.1002/jhet.349.
   Web of Science ®Google Scholar
• Inaba, S.; Ishizumi, K.; Akatsu, M.; Kume, R.; Mori, K.; Yamamoto, H. Indole derivatives JP 49004238 B 19740131. Jpn. Tokkyo Koho 1974.
   Google Scholar
• (a) Putey, A.; Fournet, G.; Joseph, B. General and Easy Access to 11-Substituted 4-Hydroxy-2,3,4,5-Tetrahydro[1,4]Diazepino[1,2-a]Indol-1-One Derivatives. Synlett 2006, 17, 2755–2758. DOI: 10.1055/s-2006-950249.
   Web of Science ®Google Scholar
  (b) Putey, A.; Popowycz, F.; Joseph, B. A Non-Classical Route to 2,3-Diiodoindoles from Indole-2-Carboxylic Acids. Synlett 2007, 3, 419–422. DOI: 10.1055/s-2007-967953.
   Web of Science ®Google Scholar
• (a) Kumar, D.; Patel, G.; Reddy, V. B. Greener and Expeditious Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Terminal Acetylenes and in Situ Generated α-Azido Ketones. Synlett 2009, 2009, 399–402. DOI: 10.1055/s-0028-1087556.
   Web of Science ®Google Scholar
  (b) Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Copper-Catalysed Multicomponent Click Synthesis of 5-Alkynyl 1,2,3-Triazoles under Ambient Conditions. Synlett 2012, 23, 2179–2182. DOI: 10.1055/s-0031-1290445.
   Web of Science ®Google Scholar
  (c) Mukherjee, N.; Ahammed, S.; Bhadra, S.; Ranu, B. C. Solvent-Free One-Pot Synthesis of 1,2,3-Triazole Derivatives by the ‘Click’ Reaction of Alkyl Halides or Aryl Boronic Acids, Sodium Azide and Terminal Alkynes over a Cu/Al2O3 Surface under Ball-Milling. Green Chem. 2013, 15, 389–397. DOI: 10.1039/C2GC36521A.
   Web of Science ®Google Scholar
  (d) Feldman, A. K.; Colasson, B.; Fokin, V. V. One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from in Situ Generated Azides. Org. Lett. 2004, 6, 3897–3899. DOI: 10.1021/ol048859z.
   PubMed Web of Science ®Google Scholar
  (e) Safa, K. D.; Mousazadeh, H. Synthesis of Novel 1,4-Disubstituted 1,2,3-Triazoles Bearing Organosilicon-Sulfur Groups via the Click Reaction Sonocatalyzed by LaCuxMn1-xO3. Synth. Commun. 2016, 46, 1595–1604. DOI: 10.1080/00397911.2016.1217339.
   Web of Science ®Google Scholar
  (f) Guo, S.; Zhou, Y.; Dai, B.; Huo, C.; Liu, C.; Zhao, Y. CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol. Synthesis 2018, 50, 2191–2199. DOI: 10.1055/s-0036-1591557.
   Web of Science ®Google Scholar
• (a) Feula, A.; Dhillon, S. S.; Byravan, R.; Sangha, M.; Ebanks, R.; Salih, M. A. H.; Spencer, N.; Male, L.; Magyary, I.; Deng, W.-P.; et al. Synthesis of Azetidines and Pyrrolidines via Iodocyclisation of Homoallyl Amines and Exploration of Activity in a Zebrafish Embryo Assay. Org. Biomol. Chem. 2013, 11, 5083–5093. DOI: 10.1039/C3OB41007B.
   PubMed Web of Science ®Google Scholar
  (b) Yi, M.; Gu, P.; Kang, X.-Y.; Sun, J.; Li, R.; Li, X.-Q. Total Synthesis of (±)-Antofine. Tetrahedron Lett. 2014, 55, 105–107. DOI: 10.1016/j.tetlet.2013.10.124.
   Web of Science ®Google Scholar
• Patonay, T.; Juhász-Tóth, E.; Bényei, A. Base‐Induced Coupling of α‐Azido Ketones with Aldehydes − an Easy and Efficient Route to Trifunctionalized Synthons 2‐Azido‐3‐Hydroxy Ketones, 2‐Acylaziridines, and 2‐Acylspiroaziridines. Eur. J. Org. Chem. 2002, 2002, 285–295. DOI: 10.1002/1099-0690(20021)2002:2 < 285::AID-EJOC285 > 3.0.CO;2-J.
   Google Scholar
• (a) Meldal, M.; Tornøe, C. W. Cu-catalyzed Azide-alkyne Cycloaddition. Chem. Rev. 2008, 108, 2952–3015. DOI: 10.1021/cr0783479.
   PubMed Web of Science ®Google Scholar
  (b) Hein, J. E.; Fokin, V. V. Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) and beyond: new Reactivity of Copper(i) Acetylides. Chem. Soc. Rev 2010, 39, 1302–1315. DOI: 10.1039/B904091A.
   PubMed Web of Science ®Google Scholar
  (c) Hassan, S.; Müller, T. J. J. Multicomponent Syntheses Based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition. Adv. Synth. Catal. 2015, 357, 617–666. DOI: 10.1002/adsc.201400904.
   Web of Science ®Google Scholar
  (d) Baltus, C. B.; Jorda, R.; Marot, C.; Berk, K.; Bazgier, V.; Krystof, V.; Prié, G.; Viaud-Massuard, M. C. Synthesis, Biological Evaluation and Molecular Modeling of a Novel Series of 7-Azaindole Based Tri-Heterocyclic Compounds as Potent CDK2/Cyclin E Inhibitors. Eur. J. Org. Chem. 2016, 108, 701–719. DOI: 10.1016/j.ejmech.2015.12.023.
   Web of Science ®Google Scholar
  (e) Camp, C.; Dorbes, S.; Picard, C.; Benoist, E. Efficient and Tunable Synthesis of New Polydentate Bifunctional Chelating Agents Using Click Chemistry. Tetrahedron Lett. 2008, 49, 1979–1983. DOI: 10.1016/j.tetlet.2008.01.086.
   Web of Science ®Google Scholar
  (f) Mishra, K. B.; Tiwari, V. K. Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles. J. Org. Chem. 2014, 79, 5752–5762. DOI: 10.1021/jo500890w.
   PubMed Web of Science ®Google Scholar
  (g) Shamim, A.; Vasconcelos, S. N. S. D.; Oliveira, I. M.; Reis, J. S.; Pimenta, D. C.; Zukerman-Schpector, J.; Stefani, H. A. Synthesis of Glycosyl Azides and Their Applications Using CuAAC Click Chemistry to Generate Bis- and Tris(Triazolyl)Glycosyl Derivatives. Synthesis 2017, 49, 5183–5196. DOI: 10.1055/s-0036-1589090.
   Web of Science ®Google Scholar
  (h) Martinelli, M.; Milcent, T.; Ongeri, S.; Crousse, B. Synthesis of New Triazole-Based Trifluoromethyl Scaffolds. Beilstein J. Org. Chem. 2008, 4, No. 19. DOI: 10.3762/bjoc.4.19.
   PubMed Web of Science ®Google Scholar
• Carcenac, Y.; David-Quillot, F.; Abarbri, M.; Duchêne, A.; Thibonnet, J. Palladium-Catalyzed Cross-Coupling of 1,4-Disubstituted 5-Iodo-1,2,3-Triazoles with Organotin Reagents. Synthesis 2013, 45, 633–638. DOI: 10.1055/s-0032-1318112.
   Web of Science ®Google Scholar
• Mayooufi, A.; Romdhani-Younes, M.; Thibonnet, J. Efficient One-Pot Synthesis of Triazole-Linked Morpholinone Scaffolds by CuAAC in the Presence of 18-Crown-6. SynOpen 2018, 2, 298–305. DOI: 10.1055/s-0037-1610399.
   Web of Science ®Google Scholar