Synthesis of dihydro-2H-spiro [acenaphthylene-1,3′-pyrazole]: An approach toward apixaban moeity

References

• (a) Rolf, H. 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chem. 1963, 2, 565–598.
   Google Scholar
  (b) Rolf, H. Kinetics and Mechanism of 1,3-Dipolar Cycloadditions. Angew. Chem. 1963, 2, 633–645.
   Google Scholar
  (c) Venkata, N. G.; Rajagopal, S. Synthesis of Spirooxindole Analogues from 2-Cyclopropyl-4-(4-Fluorophenyl)Quinoline-3-Carbaldehyde. Synth. Commun. 2019, 50, 516–525.
   Web of Science ®Google Scholar
• Albert, P. 1,3-Dipolar Cycloaddition Chemistry; John Wiley and Sons: New York, 1984; Vol. 1 and 2.
   Google Scholar
• Su, Y.; Ma, C.; Zhao, Y.; Yang, C.; Feng, Y.; Wang, K.-H.; Huang, D.; Huo, C.; Hu, Y. Regioselective Synthesis of Spiro Naphthofuranone-Pyrazoline via a [3 + 2] Cycloaddition of Benzoaurones with Nitrile Imines. Tetrahedron 2020, 76, 131355. DOI: https://doi.org/10.1016/j.tet.2020.131355.
   Web of Science ®Google Scholar
• (a) Mohammad, A.-H.; Britta, D.; Alexandra, K. K.; Ashraf, H. A.; Rolf, W. H.; Matthias, E. Discovery and Optimization of 1,3,5-Trisubstituted Pyrazolines as Potent and Highly Selective Allosteric Inhibitors of Protein Kinase C-ζ. J. Med. Chem. 2014, 15, 6513–6530.
   Google Scholar
  (b) Akranth, M.; Md. Rahmat, A.; Md. Tauquir, A.; Rikta, S.; Omprakash, T.; Mymoona, A.; Md. Shaquiquzzaman.; M. Mumtaz, A. Pyrazolines: A Biological Review. Mini-Rev. Med. Chem. 2013, 13, 921–931.
   PubMed Web of Science ®Google Scholar
  (c) Timothy, M. A.; Alpa, K.; Katie, M. V.; Cathryn, S.; John, B.; James, P. S.; Stephen, F. T.; Dennis, C. L. Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists. J. Med. Chem. 2013, 56, 6434–6456.
   PubMed Web of Science ®Google Scholar
  (d) Lahtchev, K. L.; Batovska, D. I.; Parushev, S. P.; Ubiyvovk, V. M.; Sibirny, A. A. Antifungal Activity of Chalcones: A Mechanistic Study Using Various Yeast Strains. Eur. J. Med. Chem. 2008, 43, 2220–2228.
   PubMed Web of Science ®Google Scholar
  (e) Shen-Jeu, W.; Cheng-Tsung, L.; Lo-Ti, T.; Jing-Ru, W.; Horng-Huey, K.; Jih-Pyang, W.; Chun-Nan, L. Synthetic Chalcones as Potential anti-Inflammatory and Cancer Chemopreventive Agents. Eur. J. Med. Chem. 2005, 40, 103–112.
   PubMed Web of Science ®Google Scholar
• (a) Houda, G.; Sarra, B.; Moheddine, A.; Abderrahim, K.; Michael, K.; Carsten, S.; Christopher, G.; Yoann, R.; Marek, M. K. Stoichiometry-Controlled Cycloaddition of Nitrilimines with Unsymmetrical Exocyclic Dienones: Microwave-Assisted Synthesis of Novel Mono- and Dispiropyrazoline Derivatives. RSC Adv. 2016, 6, 49868–49875.
   Web of Science ®Google Scholar
  (b) Gang, W.; Xiaohua, L.; Tianyu, H.; Yulong, K.; Lili, L.; Xiaoming, F. Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Imines for the Synthesis of Chiral Spiro-Pyrazoline-Oxindoles. Org. Lett. 2013, 15, 76–79.
   PubMed Web of Science ®Google Scholar
  (c) Anand, S.; Amanda, L. L.; Gregory, P. R. Synthesis of Oxindolyl Pyrazolines and 3-Amino Oxindole Building Blocks via a Nitrile Imine [3 + 2] Cycloaddition Strategy. Org. Lett. 2012, 14, 5266–5269.
   PubMed Web of Science ®Google Scholar
• (a) American Society of Health-System Pharmacists. Apixaban Monograph for Professionals. Drugs.com (accessed March 27, 2019).
   Google Scholar
  (b) British National Formulary: BNF 76; Pharmaceutical Press: London, UK, 2018; 76th ed., pp. 124–125.
   Google Scholar
  (c) U.S. Food and Drug Administration (FDA). FDA approves first generics of Eliquis. https://www.fda.gov/news-events/press-announcements/fda-approves-first-generics-eliquis (accessed 23 December 2019).
   Google Scholar
• Lefkaditis, D. A.; Nicolaides, D. N.; Papageorgiou, G. K.; Stephanidou-Stephanatou, J. Synthesis of Acenaphtho[1,2-x] Heterocycles and Spiro[Acenaphthylene 1-Isoxazoles]. J. Heterocycl. Chem. 1990, 27, 227–230. DOI: https://doi.org/10.1002/jhet.5570270221.
   Web of Science ®Google Scholar
• Abdolali, A.; Leila, M. A Convenient 1,3-Dipolar Cycloaddition Reaction for the Synthesis of Spirooxindoles and Some Other Spirocompounds Containing the 1,3,4-Oxadiazole Moiety. Helv. Chim. Acta 2016, 99, 457–461.
   Web of Science ®Google Scholar
• For recent examples of reactions with spiro acenaphthylene 1, 3 pyrazole, see: (a) Michail, N. E.; Alexey, I. I.; Valentina, M. M.; Pavel, A. B.; Fructuoso, B.; Belen, B. General Non-Catalytic Approach to Spiroacenaphthylene Heterocycles: Multicomponent Assembling of Acenaphthenequinone, Cyclic CH-Acids and Malononitrile. Tetrahedron 2012, 68, 5833–5837. (b) Minoo, D.; Zeinab, Noroozi, T.; Mohsen, N.; Ayoob, B. Organic Reaction in Water: A Highly Efficient and Environmentally Friendly Synthesis of Spiro Compounds Catalyzed by L- Proline. Helv. Chim. Acta 2011, 94, 824–830. (c) Mina, S.; Majid, M. H.; Yahya, S. B.; Hossein, A. O. One-Pot Three-Component Synthesis of the Spiroacenaphthylene Derivatives. Tetrahedron 2010, 66, 5345–5348.
   Web of Science ®Google Scholar
• Preparation of dipolarophile: (a) Jomon, P. J.; Christy, K.; Sajitha, L. U.; Roshini, K. T.; Rakesh, K.; Nidhisha, V.; Perupparampil, A. U.; Sreedharan, P. Domino Reaction Sequences Leading to the Formation of 2:2 Adducts between Acenaphthenequinone and Acetophenone. ARKIVOC 2014, 2014, 127–138. DOI: https://doi.org/10.3998/ark.5550190.p008.834. (b) Giuseppe, F.; Mariella, M.; PierPaolo, R.; Gianfranco, T. An Easy Lewis Acid-Mediated Isomerization from (E)- to (Z)-Oxoindolin-3-Ylidene Ketones. Tetrahedron 1994, 50, 10955–10962. (c) Demetrics, A. L.; Nicolaos, G. A.; Demetrios, N. N. Preparation and Catalytic Hydrogenation of Spiro[Acenaphthylene-Dioxazoles] and Spiro[Acenaphthylene-Isoxazoles]. Liebigs Ann. Chem. 1986, 11, 1863–1871. (d) Tsuge, O.; Tashiro, M.; Shinkai, I. Studies of Acenaphthene Derivatives. XVI. The Wittig Reaction with Acenaphthenequinone. BCSJ. 1969, 42, 181–185. DOI: https://doi.org/10.1246/bcsj.42.181. . (e) Srinu, L.; Sathiah, T.; Paramasivan, T. P. Facile Synthesis of Novel Dispiroheterocylic Derivatives through Cycloaddition of Azomethine Ylides with Acenaphthenone-2-Ylidine Ketones. Tetrahedron Lett. 2012, 53, 7052–7055.
   Web of Science ®Google Scholar
• Preparation of hydrazonoyl Chlorides: (a) Donald, J. P. P.; Michael, J. O.; Stephanie, K.; Karen, A. R.; Richard, S. A.; Angela, S.; Pancras, C. W.; Alan, R. R.; Joseph, M. L.; Robert, M. K.; et al. Discovery of 1-(4-Methoxyphenyl)-7-Oxo-6-(4-(2-Oxopiperidin-1-yl)Phenyl)-4,5,6,7-Tetrahydro- 1H-Pyrazolo[3,4-c]Pyridine-3-Carboxamide (Apixaban, BMS-562247), a Highly Potent, Selective, Efficacious, and Orally Bioavailable Inhibitor of Blood Coagulation Factor Xa. J. Med. Chem. 2007, 50, 5339–5356. (b) Ju, L.; Minhua, N.; Yanjing, W.; Jinxing, H.; Feng, Z.; Yanlin, G.; Yajing, L.; Ping, G. Design, Synthesis and Structure-Activity Relationships of Novel 4-Phenoxyquinoline Derivatives Containing 1,2,4-Triazolone Moiety as c-Met Kinase Inhibitors. Eur. J. Med. Chem. 2016, 123, 431–446. (c) Yong, W.; Xiaoqing, S.; Di, Y.; Zhuang, G.; Xuxu, F.; Minhua, N.; Feng, Z.; Yue, L.; Yue, L.; Yulin, W.; et al. Design, Synthesis, and Structure–Activity Relationship of Novel and Effective Apixaban Derivatives as FXa Inhibitors Containing 1,2,4-Triazole/Pyrrole Derivatives as P2 Binding Element. Bioorg. Med. Chem. 2016, 24, 5646–5661.
   Google Scholar
  (d) Virgili-Bernado, M.; Alonso-Xalma, M.; Almansa-Rosales, C.; José, L. Meta Substituted Phenylpyrazolo-and Phenylpyrrolo-Pyridazine Derivatives Having Multimodal Activity Against Pain. Esteve pharmaceuticals: Barcelona, Spain, 2018.
   Google Scholar
  (e) Lucia, S.; Matteo, F.; Daniela, C.; Flavia, V.; Marco, B.; Katia, V.; Fabrizio, V.; Diego, D. B.; Catia, L.; Rosaria, V.; Vittoria, C. Exploring the 2- and 5-Positions of the Pyrazolo[4,3-d]Pyrimidin-7-Amino Scaffold to Target Human A1 and A2A Adenosine Receptors. Bioorg. Med. Chem. 2016, 24, 2794–2808.
   PubMed Web of Science ®Google Scholar
  (f) Youyi, P.; Qiang, Z.; Sonia, A.; Susan, M. K.; Sandhya, K.; Kenneth, M. W.; Richard, D. H.; William, J. W. Novel Delta Opioid Receptor Agonists Exhibit Differential Stimulation of Signaling Pathways. Bioorg Med. Chem. 2009, 17, 6442–6450.
   PubMed Web of Science ®Google Scholar
  (g) Yingpeng, S.; Yanan, Z.; Bingbing, C.; Xiaolong, Z.; Rong, Z.; Xuan, L.; Danfeng, H.; Ke-Hu, W.; Congde, H.; Yulai, H. [3 + 2] Cycloaddition of Para-Quinone Methides with Nitrile Imines: Approach to Spiro-Pyrazoline-Cyclohexadienones. J. Org. Chem. 2019, 84, 6719–6728.
   PubMed Web of Science ®Google Scholar