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Synthesis of 2,3-diaryl-2,3,4,4а-tetrahydro-5Н-indeno[1,2-c]pyridazin-5-ones

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 1,3-indanedione-derived donor-acceptor cyclopropanes with phenylhydrazine in the presence of catalytic amounts of scandium trifluoromethanesulfonate leads to the formation of indeno[1,2-c]pyridazine derivatives.

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References

  1. Tomilov, Y. V.; Menchikov, L. G.; Novikov, R. A.; Ivanova, O. A.; Trushkov, I. V. Russ. Chem. Rev. 2018, 87, 201. [Usp. Khim. 2018, 87, 201.]

    Article  CAS  Google Scholar 

  2. (a) Isr. J. Chem. 2016, 6-7, Special Issue: Chemistry of DonorAcceptor Cyclopropanes and Cyclobutanes. a Schneider, T. F.; Kaschel, J.; Werz, D. B. Angew. Chem., Int. Ed. 2014, 53, 5504. b Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.

  3. (a) Grover, H. K.; Emmett, M. R.; Kerr, M. A. Org. Biomol. Chem. 2015, 13, 655. (b) Novikov, R. A.; Tomilov, Y. V. Mendeleev Commun. 2015, 25, 1. (c) Di Grandi, M. J. Org. Biomol. Chem. 2014, 12, 5331. (d) Cavitt, M. A.; Phun, L. H.; France, S. Chem. Soc. Rev. 2014, 43, 804. (e) Mel'nikov, M. Ya.; Budynina, E. M.; Ivanova, O. A.; Trushkov, I. V. Mendeleev Commun. 2011, 21, 293.

  4. (a) Pagenkopf, B. L.; Vemula, N. Eur. J. Org. Chem. 2017, 2561. (b) Kumar, I. RSC Adv. 2014, 4, 16397. (c) Campbell, M. J.; Johnson, J. S.; Parsons, A. T.; Pohlhaus, P. D.; Sanders, S. D. J. Org. Chem. 2010, 75, 6317.

  5. (a) Verma, K.; Banerjee, P. Adv. Synth. Catal. 2018, 360, 3687. (b) Qian, S.; Xie, Z.; Liu, J.; Li, M.; Wang, S.; Luo, N.; Wang, C. J. Org. Chem. 2018, 83, 14768. (c) Zhang, J.; Jiang, H.; Zhu, S. Adv. Synth. Catal. 2017, 359, 2924. (d) Villemson, E. V.; Budynina, E. M.; Ivanova, O. A.; Skvortsov, D. A.; Trushkov, I. V.; Melnikov, M. Ya. RSC Adv. 2016, 6, 62014. (e) Xiao, J.-A.; Li, J.; Xia, P.-Y.; Zhou, Z.-F.; Deng, Z.-X.; Xiang, H.-Y.; Chen, X.-Q.; Yang, H. J. Org. Chem. 2016, 81, 11185. (f) Liu, C.; Zhou, L.; Huang, W.; Wang, M.; Gu, Y. Tetrahedron 2016, 72, 563.

  6. (a) Gharpure, S. J.; Nanda, L. N. Tetrahedron Lett. 2017, 58, 711. (b) Tang, P.; Qin, Y. Synthesis 2012, 2969. (c) Wang, Z. Synlett 2012, 2311. (d) Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051. (e) O'Connor, N. R.; Wood, J. L.; Stolz, B. M. Isr. J. Chem. 2016, 56, 431.

  7. (a) Dey, R.; Kumar, P.; Banerjee, P. J. Org. Chem. 2018, 83, 5438. (b) Chagarovskiy, A. O.; Ivanova, O. A.; Shumsky, A. N.; Trushkov, I. V. Chem. Heterocycl. Compd. 2017, 53, 1220. [Khim. Geterotsikl. Soedin. 2017, 53, 1220.] (c) Gladow, D.; Reissig, H.-U. Helv. Chim. Acta 2012, 95, 1818. c Reichelt, I.; Reissig, H.-U. Synthesis 1984, 786.

  8. (a) Sathishkannan, G.; Tamilarasan, V. J.; Srinivasan, K. Org. Biomol. Chem. 2017, 15, 1400. (b) Xue, S.; Liu, J.; Qing, X.; Wang, C. RSC Adv. 2016, 6, 67724. (с) Cao, W.; Zhang, H.; Chen, J.; Deng, H.; Shao, M.; Lei, L.; Qian, J.; Zhu, Y. Tetrahedron 2008, 64, 6670.

  9. (a) Braun, J.; Ariens, M. I.; Matsuo, B. T.; de Vries, S.; van Wordragen, E. D. H.; Ellenbroek, B. D.; Vande Velde, C. M. L.; Orru, R. V. A.; Ruijter, E. Org. Lett. 2018, 20, 6611. (b) El-Kholy, I. E.-S.; Fuid-Alla, H. M.; Mishrikey, M. M. J. Heterocycl. Chem. 1980, 17, 541. (c) Sasaki, T.; Eguchi, S.; Ohno, M.; Umemura, T. J. Org. Chem. 1973, 38, 4095.

  10. (a) Salikov, R. F.; Trainov, K. P.; Belousova, I. K.; Belyy, A. Yu.; Fatkullina, Y. Sh.; Mulyukova, R. V.; Zainullina, L. F.; Vakhitova, Y. V.; Tomilov, Y. V. Eur. J. Med. Chem. 2018, 144, 211. (b) Salikov, R. F.; Trainov, K. P.; Levina, A. A.; Belousova, I. K.; Medvedev, M. G.; Tomilov, Y. V. J. Org. Chem. 2017, 82, 790.

  11. Ivanov, K. L.; Villemson, E. V.; Budynina, E. M.; Ivanova, O. A.; Trushkov, I. V.; Melnikov, M. Ya. Chem.– Eur. J. 2015, 21, 4975.

    Article  CAS  PubMed  Google Scholar 

  12. (a) Toma, L.; Cignarella, G.; Barlocco, D.; Ronchetti, F. J. Med. Chem. 1990, 33, 1591. (b) Cignarella, G.; Barlocco, D.; Pinna, G. A.; Loriga, M.; Tofanetti, O.; Germini, M.; Sala, F. J. Med. Chem. 1986, 29, 2191. (c) Sircar, I.; Duell, B. L.; Cain, M. H.; Burke, S. E.; Bristol, J. A. J. Med. Chem. 1986, 29, 2142.

  13. Masciocchi, D.; Gelain, A.; Porta, F.; Meneghetti, F.; Pedretti, A.; Celentano, G.; Barlocco, D.; Legnani, L.; Toma, L.; Kwon, B.-M.; Asai, A.; Villa, S. MedChemComm 2013, 4, 1181.

    Article  CAS  Google Scholar 

  14. (a) Niculescu-Duvaz, D.; Niculescu-Duvaz, I.; Suijkerbuijk, B. M. J. M.; Menard, D.; Zambon, A.; Nourry, A.; Davies, L.; Manne, H. A.; Friedlos, F.; Ogilvie, L.; Hedley, D.; Takle, A. K.; Wilson, D. M.; Pons, J.-F.; Coulter, T.; Kirk, R.; Cantarino, N.; Whittaker, S.; Marais, R.; Springer, C. J. Bioorg. Med. Chem. 2010, 18, 6934. (b) Campagna, F.; Palluotto, F.; Carotti, A.; Casini, G.; Genchi, G. Bioorg. Med. Chem. 1999, 7, 1533. (c) Barlocco, D.; Bergomi, M.; Menta, E.; Palumbo, M.; Cignarella, G. Recl. Trav. Chim. Pays-Bas 1996, 115, 25. (d) Bakewell, S. J.; Coates, W. J.; Comer, M. B.; Reeves, M. L.; Warrington, B. H. Eur. J. Med. Chem. 1990, 25, 765. (e) Moos, W. H.; Humblet, C. C.; Sircar, I.; Rithner, C.; Weishaar, R. E.; Bristol, J. A.; McPhail, A. T. J. Med. Chem. 1987, 30, 1963.

  15. (a) Carotti, A.; Catto, M.; Leonetti, F.; Campagna, F.; SotoOtero, R.; Mendez-Alvarez, E.; Thull, U.; Testa, B.; Altomare, C. J. Med. Chem. 2007, 50, 5364. (b) Novaroli, L.; Daina, A.; Favre, E.; Bravo, J.; Carotti, A.; Leonetti, F.; Catto, M.; Carrupt, P.-A.; Reist, M. J. Med. Chem. 2006, 49, 6264. (c) Frederick, R.; Dumont, W.; Ooms, F.; Aschenbach, L.; Van der Schyf, C. J.; Castagnoli, N.; Wouters, J.; Krief, A. J. Med. Chem. 2006, 49, 3743. (d) Altomare, C.; Cellamare, S.; Summo, L.; Catto, M.; Carotti, A.; Thull, U.; Carrupt, P.-A.; Testa, B.; Stoeckli-Evans, H. J. Med. Chem. 1998, 41, 3812.

  16. Ivanova, O. A.; Chagarovskiy, A. O.; Shumsky, A. N.; Krasnobrov, V. D.; Levina, I. I.; Trushkov, I. V. J. Org. Chem. 2018, 83, 543.

    Article  CAS  PubMed  Google Scholar 

  17. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.

    Article  CAS  Google Scholar 

  18. Bastiansen, O.; Fritsch, F. N.; Hedberg, K. Acta Crystallogr. 1964, 17, 538.

    Article  CAS  Google Scholar 

  19. (a) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Fringuelli, F.; Mantellini, F.; Matteucci, M.; Piermatti, O.; Pizzo, F. Helv. Chim. Acta 2001, 84, 513. (b) Sucrow, W.; Ellermann, K.-H.; Flörke, U.; Haupt, H.-J. Chem. Ber. 1988, 121, 2007. (c) Sommer, S. Tetrahedron Lett. 1977, 18, 117. (d) Tomilov, Yu. V.; Platonov, D. N.; Averkiev, B. B.; Shulishov, E. V.; Nefedov, O. M. Russ. Chem. Bull., Int. Ed. 2003, 52, 187. [Izv. Akad. Nauk, Ser. Khim. 2003, 176.]

  20. Qian, P.; Du, B.; Song, R.; Wu, X.; Mei, H.; Han, J.; Pan, Y. J. Org. Chem. 2016, 81, 6546.

    Article  CAS  PubMed  Google Scholar 

  21. Nambu, H.; Fukumoto, M.; Hirota, W.; Ono, N.; Yakura, T. Tetrahedron Lett. 2015, 56, 4312.

    Article  CAS  Google Scholar 

  22. Rosenfeld, M. J.; Ravi Shankar, B. K.; Shechter, H. J. Org. Chem. 1988, 53, 2699.

    Article  CAS  Google Scholar 

  23. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found Crystallogr. 2015, 71, 3.

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This work was supported by the Russian Science Foundation (grant 18-13-00449).

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Authors and Affiliations

  1. Dmitry Rogachev Federal Research Center of Pediatric Hematology, Oncology and Immunology, 1 Samory Mashela St., Moscow, 117997, Russia

    Alexey O. Chagarovskiy & Igor V. Trushkov

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Alexey O. Chagarovskiy, Elena D. Strel’tsova & Igor V. Trushkov

  3. Lomonosov Moscow State University, 1 Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Victor B. Rybakov

  4. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow, 119334, Russia

    Irina I. Levina

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  1. Alexey O. Chagarovskiy
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  2. Elena D. Strel’tsova
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  3. Victor B. Rybakov
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  4. Irina I. Levina
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  5. Igor V. Trushkov
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Correspondence to Igor V. Trushkov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 240–245

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Chagarovskiy, A.O., Strel’tsova, E.D., Rybakov, V.B. et al. Synthesis of 2,3-diaryl-2,3,4,4а-tetrahydro-5Н-indeno[1,2-c]pyridazin-5-ones. Chem Heterocycl Comp 55, 240–245 (2019). https://doi.org/10.1007/s10593-019-02448-y

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  • DOI: https://doi.org/10.1007/s10593-019-02448-y

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