Skip to main content
SpringerLink
Log in

Regioselectivity of (3+2) cycloaddition of azomethine ylides to activated olefins in the synthesis of spiro[oxindole-3,2′-pyrrolidine] derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The effect of the structure of the starting compounds on the regioselectivity of the (3+2) cycloaddition of azomethine ylides to olefins activated by electron-withdrawing groups in the synthesis of spiro[oxindole-3,2′-pyrrolidine] derivatives is generalized and analyzed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1.
Figure 2.

Similar content being viewed by others

References

  1. (a) Liu, Y.; Wang, H.; Wan, J. Asian J. Org. Chem.2013, 2, 374. (b) Moradi, R.; Ziarani, G. M.; Lashgari, N. ARKIVOC2017, (i), 148. (c) Lashgari, N.; Ziarani, G. M. ARKIVOC2012, (i), 277. (d) Borad, M. A.; Bhoi, M. N.; Prajapati, N. P.; Patel, H. D. Synth. Commun.2014, 44, 1043.

  2. Jossang, A.; Jossang, P.; Hadi, H. A.; Sévenet, T.; Bodo, B. J. Org. Chem.1991, 56, 6527.

    Article  CAS  Google Scholar 

  3. Anderton, N.; Cockrum, P. A.; Colegate, S. M.; Edgar, J. A.; Flower, K.; Vit, I.; Willing, R. I. Phytochem.1998, 48, 437.

    Article  CAS  Google Scholar 

  4. Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron1996, 52, 12651.

    Article  CAS  Google Scholar 

  5. (a) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc.2005, 127, 10130. (b) Zhao, Y.; Bernard, D.; Wang, S. BioDiscovery2013, 8, e8950.

  6. (a) Cheng, P.; Guo, W.; Chen, P.; Liu, Y.; Du, X.; Li, C. Chem. Commun.2016, 52, 3418. (b) Snieckus, V.; Richardson, P. Synfacts2019, 15, 0593. (c) Anis'kov, A.; Klochkova, I.; Tumskiy, R.; Yegorova, A. Molecules2017, 22, 2134. (d) Akaev, A. A.; Bezzubov, S. I.; Desyatkin, V. G.; Vorobyeva, N. S.; Majouga, A. G.; Melnikov, M. Ya.; Budynina, E. M. J. Org. Chem.2019, 84, 3340.

  7. (a) Izmest'ev, A. N.; Gazieva, G. A.; Sigay, N. V.; Serkov, S. A.; Karnoukhova, V. A.; Kachala, V. V.; Shashkov, A. S.; Zanin, I. E.; Kravchenko, A. N.; Makhova, N. N. Beilstein J. Org. Chem.2016, 12, 2240. (b) Rao, J. N. S.; Raghunathan, R. Tetrahedron Lett.2012, 53, 854. (c) Taghizadeh, M. J.; Arvinnezhad, H.; Samadi, S.; Jadidi, K.; Javidan, A.; Notash, B. Tetrahedron Lett.2012, 53, 5148. (d) Gazieva, G. A.; Kolotyrkina, N. G.; Kravchenko, A. N.; Makhova, N. N. Russ. Chem. Bull., Int. Ed.2014, 63, 431. [Izv. Akad. Nauk, Ser. Khim.2014, 431.] (e) Ren, D.; Hu, X.; Li, X. Chem. Heterocycl. Compd.2019, 55, 275. [Khim. Geterotsikl. Soedin.2019, 55, 275.] (f) Taghizadeh, M. J.; Arvinnezhad, H.; Samadi, S.; Jadidi, K.; Javidan, A.; Notash, B. Tetrahedron Lett.2012, 53, 5148. (g) Korotaev, V. Yu.; Zimnitskiy, N. S.; Barkov, A. Yu.; Kutyashev, I. B.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd.2018, 54, 905. [Khim. Geterotsikl. Soedin.2018, 54, 905.]

  8. (a) Ito, M.; Iwatani, M.; Yamamoto, T.; Tanaka, T.; Kawamoto, T.; Morishita, D.; Nakanishi, A.; Maezaki, H. Bioorg. Med. Chem.2017, 25, 4753. (b) Rehn, S.; Bergman, J.; Stensland, B. Eur. J. Org. Chem.2004, 413. (c) Malini, K.; Periyaraja, S.; Shanmugam, P. Eur. J. Org. Chem.2017, 3774.

  9. (a) Pavlovskaya, T. L.; Lipson, V. V.; Yaremenko, F. G.; Musatov, V. I. Russ. J. Org. Chem.2013, 49, 1712. [Zh. Org. Khim.2013, 49, 1728.] (b) Pavlovskaya, T. L.; Yaremenko, F. G.; Lipson, V. V.; Shishkina, S. V.; Shishkin, O. V.; Musatov, V. I.; Karpenko, A. S. Beilstein J. Org. Chem.2014, 10, 117. (c) Shukla, D.; Babu, S. A. Adv. Synth. Catal.2019, 361, 2075.

  10. (a) Fokas, D.; Ryan, W. J.; Casebier, D. S.; Coffen, D. L. Tetrahedron Lett.1998, 39, 2235. (b) Song, Q.; An, X.; Che, F.; Shen, T. J. Heterocycl. Chem.2015, 52, 1496. (c) Revathy, K.; Lalitha, A. RSC Adv.2014, 4, 279. (d) Zhao, P.; Bai, L.; Ma, J.; Zeng, Y.; Li, L.; Zhang, Y.; Lu, C.; Dai, H.; Wu, Z.; Li, Y.; Wu, X.; Chen, G.; Hao, X.; Shen, Y.; Deng, Z.; Floss, H. G. Chem. Biol.2008, 15, 863. (e) Sharma, R.; Sapnakumari, M.; Narayana, B.; Sarojini, B. K.; Gupta, V. K.; Kant, R. Eur. Chem. Bull.2014, 3, 183. (f) Wu, G.; Ouyang, L.; Liu, J.; Zeng, S.; Huang, W.; Han, B.; Wu, F.; He, G.; Xiang, M. Mol. Diversity2013, 17, 271. (g) Kanagaraju, G.; Thangamani, A. Orient. J. Chem.2014, 30, 1619. (h) Sharma, P.; Sapnakumari, M.; Narayana, B.; Sarojini, B. K.; Kant, R. Chem. Sci. Trans.2015, 4, 1037. (i) Hussein, E. M.; Moussa, Z.; El Guesmi, N.; Ahmed, S. A. RSC Adv.2018, 8, 24116. (j) Chen, G.; He, H.-P.; Ding, J.; Hao, X.-J. Heterocycl. Commun.2009, 15, 355.

  11. Klochkova, I. N.; Shchekina, M. P.; Anis'kov, A. A. Chem. Heterocycl. Compd.2014, 50, 479. [Khim. Geterotsikl. Soedin.2014, 527.]

  12. (a) Bakthadoss, M.; Sivakumar, N. Synlett2011, 1296. (b) Poornachandran, M.; Muruganantham, R.; Raghunathan, R. Synth. Commun.2006, 36, 141. (c) Bakthadoss, M.; Sivakumar, N.; Devaraj, A.; Sharada, D. S. Synthesis2011, 2136. (d) Bakthadoss, M.; Sivakumar, N. Synlett2009, 1014. (e) Gollner, A.; Rudolph, D.; Arnhof, H.; Bauer, M.; Blake, S. M.; Boehmelt, G.; Karolyi-Oezguer, J.; Cockroft, X.-L.; Dahmann, G.; Ettmayer, P.; Gerstberger, T.; Karolyi-Oezguer, J.; Kessler, D.; Kofink, C.; Ramharter, J.; Rinnenthal, J.; Savchenko, A.; Schnitzer, R.; Weinstabl, H.; Weyer-Czernilofsky, U.; Wunberg, T.; McConnell, D. B. J. Med. Chem.2016, 59, 10147. (f) Mali, P. R.; Rao, L. C.; Bangade, V. M.; Shirsat, P. K.; George, S. A.; Jagadeesh babu, N.; Meshram, H. M. New J. Chem.2016, 40, 2225. (g) Rajesh, S. M.; Perumal, S.; Menéndez, J. C.; Yogeeswari, P.; Sriram, D. MedChemComm2011, 2, 626. (h) Chen, G.; Yang, J.; Gao, S.; He, H.; Li, S.; Di, Y.; Chang, Y.; Lu, Y.; Hao, X. Mol. Diversity2012, 16, 151. (i) Sundar, J. K.; Rajesh, S. M.; Sivamani, J.; Perumal, S.; Natarajan, S. Chem. Cent. J.2011, 5, 45. (j) Ramharter, J.; Broeker, J.; Gille, A.; Gollner, A.; Henry, M.; Toelle, N.; Weinstabl, H. WO Patent 2016026937. (k) Arumugam, N.; Almansour, A. I.; Kumar, R. S.; Periasamy, V. S.; Athinarayanan, J.; Alshatwi, A. A.; Govindasami, P.; Altaf, M.; Menéndez, J. C. Tetrahedron2018, 74, 5358.

  13. (a) Galvis, C. E. P.; Kouznetsov, V. V. Org. Biomol. Chem.2013, 11, 7372. (b) Chen, G.; Miao, Y.-Q.; Zhou, R.; Zhang, L.; Zhang, J.; Hao, X.-J. Res. Chem. Intermed.2013, 39, 2445. (c) Gayen, B.; Banerji, A. Monatsh. Chem.2014, 145, 1953. (d) Alimohammadi, K.; Sarrafi, Y.; Tajbakhsh, M.; Yeganegi, S.; Hamzehloueian, M. Tetrahedron2011, 67, 1589.

  14. (a) Wang, Y.-C.; Wang, J.-L.; Burgess, K. S.; Zhang, J.-W.; Zheng, Q.-M.; Pu, Y.-D.; Yan, L.-J.; Chen, X.-B. RSC Adv.2018, 8, 5702. (b) Chornous, V. A.; Mel'nik, O. Ya.; Mel'nik, D. A.; Rusanov, E. B.; Vovk, M. V. Russ. J. Org. Chem.2015, 51, 1423. [Zh. Org. Khim.2015, 51, 1454.]

  15. Barkov, A. Yu.; Zimnitskiy, N. S.; Korotaev, V. Yu.; Kutyashev, I. B.; Moshkin, V. S.; Sosnovskikh, V. Ya. Tetrahedron2016, 72, 6825.

    Article  CAS  Google Scholar 

  16. Barkov, A. Yu.; Zimnitskiy, N. S.; Kutyashev, I. B.; Korotaev, V. Yu.; Moshkin, V. S.; Sosnovskikh, V. Ya. J. Fluorine Chem.2017, 204, 37.

    Article  CAS  Google Scholar 

  17. (a) Sustmann, R. Pure Appl. Chem.1974, 40, 569. (b) Raj, A. A.; Raghunathan, R.; Malar, E. J. P. Heteroat. Chem.1999, 10, 500. (c) Fukui, K. Acc. Chem. Res.1971, 4, 57. (d) Verma, S.; George, J.; Singh, S.; Pardasani, P.; Pardasani, R. Org. Med. Chem. Lett.2011, 1, 6.

  18. (a) Houk, K. N.; Sims, J.; Duke, R. E.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc.1973, 95, 7287. (b) Pérez, P.; Domingo, L. R.; Aurell, M. J.; Contreras, R. Tetrahedron2003, 59, 3117. (c) Chen, G.; Yang, J.; Gao, S.; Zhang, Y.; Hao, X. Res. Chem. Intermed.2015, 41, 4987.

  19. (a) Tiwari, K. N.; Pandurang, T. P.; Pant, S.; Kumar, R. Tetrahedron Lett.2016, 57, 2286. (b) Faraji, L.; Arvinnezhad, H.; Alikami, N.; Jadidi, K. Lett. Org. Chem.2010, 7, 472. (c) Sudhakara, A.; Kumar, H. C. K.; Jayadevappa, H.; Mahadevan, K. M. Org. Chem. Ind. J.2012, 8, 94. (d) Pardasani, P.; Pardasani, R. T.; Sherry, D.; Chaturvedi, V. Synth. Commun.2002, 32, 435. (e) Coulter, T.; Grigg, R.; Malone, J. F.; Sridharan, V. Tetrahedron Lett.1991, 32, 5417.

  20. Prasad, T. A. A.; Vithiya, B. S. M.; Ignacimuthu, S. Pharma Chem.2011, 3, 293.

    CAS  Google Scholar 

  21. Wang, H.-J.; Pan, B.-W.; Zhang, W.-H.; Yang, C.; Liu, X.-L.; Zhao, Z.; Feng, T.-T.; Zhou, Y.; Yuan, W.-C. Tetrahedron2015, 71, 8131.

    Article  CAS  Google Scholar 

  22. Tiwari, K. N.; Pandurang, T. P; Pant, S.; Sreelekha, P. Synth. Commun.2018, 48, 802.

  23. Dandia, A.; Khan, S.; Soni, P.; Indora, A.; Mahawar, D. K.; Pandya, P.; Chauhan, C. S. Bioorg. Med. Chem. Lett.2017, 27, 2873.

    Article  CAS  Google Scholar 

  24. Rezaei, S. J. T.; Nabid, M. R.; Yari, A.; Ng, S. W. Ultrason. Sonochem.2011, 18, 49.

    Article  Google Scholar 

  25. Taghizadeh, M. J.; Jadidi, K. Iran. Chem. Commun.2015, 3, 67.

    CAS  Google Scholar 

  26. (a) Pavlovskaya, T. L.; Red'kin, R. G.; Yaremenko, F. G.; Shishkina, S. V.; Shishkin, O. V.; Musatov, V. I.; Lipson, V. V. Chem. Heterocycl. Compd.2013, 49, 882. [Khim. Geterotsikl. Soedin.2013, 945.] (b) Girgis, A. S.; Stawinski, J.; Ismail, N. S.; Farag, H. Eur. J. Med. Chem.2012, 47, 312. (c) Bhaskar, G.; Arun, Y.; Balachandran, C.; Saikumar, C.; Perumal, P. T. Eur. J. Med. Chem.2012, 51, 79. (d) Chen, H.; Wang, S.-Y.; Xu, X.-P.; Ji, S.-J. Synth. Commun.2011, 41, 3280. (e) Dandia, A.; Jain, A. K.; Laxkar, A. K. Tetrahedron Lett.2013, 54, 3929. (f) Dandia, A.; Jain, A. K.; Sharma, S.; Singh, R. J. Heterocycl. Chem.2018, 55, 1419. (g) Bakthadoss, M.; Sivakumar, N.; Devaraj, A. Tetrahedron Lett.2015, 56, 4980. (h) Nayak, S.; Mishra, S. K.; Bhakta, S.; Panda, P.; Baral, N.; Mohapatra, S.; Purohit, C. S.; Satha, P. Lett. Org. Chem.2016, 13, 11. (i) Naga Siva Rao, J.; Raghunathan, R. Tetrahedron Lett.2013, 54, 6568. (j) Wu, S.; Zhu, G.; Wei, S.; Chen, H.; Qu, J.; Wang, B. Org. Biomol. Chem.2018, 16, 807. (k) Kutyashev, I. B.; Barkov, A. Yu.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd.2019, 55, 529. [Khim. Geterotsikl. Soedin.2019, 55, 529.] (l) Sun, Q.; Li, X.; Su, J.; Zhao, L.; Ma, M.; Zhu, Y.; Zhao, Y.; Zhu, R.; Yan, W.; Wang, K.; Wang, R. Adv. Synth. Catal.2015, 357, 3187. (m) Yue, G.; Wu, Y.; Dou, Z.; Chen, H.; Yin, Z.; Song, X.; He, C.; Wang, X.; Feng, J.; Zhang, Z.; Zou, P.; Lu, C. New J. Chem.2018, 42, 20024. (n) Xiao, J.-A.; Liu, Q.; Ren, J.-W.; Liu, J.; Carter, R. G.; Chen, X.-Q.; Yang, H. Eur. J. Org. Chem.2014, 5700. (o) Bharitkar, Y. P.; Kanhar, S.; Suneel, N.; Mondal, S. K.; Hazra, A.; Mondal, N. B. Mol. Diversity2015, 19, 251. (p) Rajkumar, V.; Aslam, N. A.; Reddy, C.; Babu, S. A. Synlett2012, 549. (q) Barman, P. D.; Sanyal, I.; Mandal, S. B.; Banerjee, A. K. Synthesis2011, 3563. (r) Prasanna, R.; Purushothaman, S.; Raghunathan, R. Tetrahedron Lett.2014, 55, 6631. (s) Ghandi, M.; Taheri, A.; Abbasi, A. Tetrahedron2010, 66, 6744. (t) Lanka, S.; Thennarasu, S.; Perumal, P. T. Tetrahedron Lett.2014, 55, 2585.

  27. Naga Siva Rao, J.; Raghunathan, R. Tetrahedron Lett.2015, 56, 2276.

  28. Weinstabl, H.; Gollner, A.; Ramharter, J.; Wunberg, T. US Patent 20160000764.

  29. (a) Izmest'ev, A. N.; Vasileva, D. A.; Melnikova, E. K.; Kolotyrkina, N. G.; Borisova, I. A.; Kravchenko, A. N.; Gazieva, G. A. New J. Chem.2019, 43, 1038. (b) Izmest'ev, A. N.; Kim, N. A.; Karnoukhova, V. A.; Kolotyrkina, N. G.; Kravchenko, A. N.; Gazieva, G. A. ChemistrySelect2019, 4, 10483. (c) Gazieva, G. A.; Izmest'ev, A. N.; Anikina, L. V.; Pukhov, S. A.; Meshchaneva, M. E.; Khakimov, D. V.; Kolotyrkina, N. G.; Kravchenko, A. N. Mol. Diversity2018, 22, 585.

  30. (a) Sridhar, G.; Gunasundari, T.; Raghunathan, R. Tetrahedron Lett.2007, 48, 319. (b) Raj, A. A.; Raghunathan, R. Synth. Commun.2003, 33, 421. (c) Raj, A. A.; Raghunathan, R.; SrideviKumari, M. R.; Raman, N. Bioorg. Med. Chem.2003, 11, 407. (d) Poornachandran, M.; Jayagobi, M.; Raghunathan, R. Synth. Commun.2010, 40, 551. (e) Poornachandran, M.; Jayagobi, M; Raghunathan, R. J. Chem. Res.2009, 240.

  31. (a) Karthikeyan, K.; Sivakumar, P. M.; Doble, M.; Perumal, P. T. Eur. J. Med. Chem.2010, 45, 3446. (b) Liu, H.; Zou, Y.; Hu, Y.; Shi, D.-Q. J. Heterocycl. Chem.2011, 48, 877. (c) Murugan, R.; Anbazhagan, S.; Sriman Narayanan, S. Eur. J. Med. Chem.2009, 44, 3272. (d) Beloglazkina, A. A.; Karpov, N. A.; Mefedova, S. R.; Polyakov, V. S.; Skvortsov, D. A; Kalinina, M. A.; Tafeenko, V. A.; Majouga, A. G.; Zyk, N. V.; Beloglazkina, E. K. Russ. Chem. Bull., Int. Ed.2019, 68, 1006. [Izv. Akad. Nauk, Ser. Khim.2019, 1006.] (e) Kaur, A.; Kaur, M.; Singh, B. J. Heterocycl. Chem.2015, 52, 827. (f) Ponnala, S.; Kumar, R.; Maulik, P. R.; Sahu, D. P. J. Heterocycl. Chem.2006, 43, 1635.

  32. (a) Boudriga, S.; Haddad, S.; Askri, M.; Soldera, A.; Knorr, M.; Strohmann, C.; Golz, C. RSC Adv.2019, 9, 11082. (b) Haddad, S.; Boudriga, S.; Porzio, F.; Soldera, A.; Askri, M.; Knorr, M.; Rousselin, Y.; Kubicki, M. M.; Golz, C.; Strohmann, C. J. Org. Chem.2015, 80, 9064.

  33. (a) Kurbatov, S. V.; Zarubaev, V. V.; Karpinskaya, L. A.; Shvets, A. A.; Kletsky, M. E.; Burov, O. N.; Morozov, P. G.; Kiselev, O. I.; Minkin, V. I. Russ. Chem. Bull., Int. Ed.2014, 63, 1130. [Izv. Akad. Nauk, Ser. Khim.2014, 1130.] (b) Haddad, S.; Boudriga, S.; Porzio, F.; Soldera, A.; Askri, M.; Sriram, D.; Yogeeswari, P.; Knorr, M.; Rousselin, Y.; Kubicki, M. M. RSC Adv.2014, 4, 59462. (c) Hu, Y.; Zou, Y.; Wu, H.; Shi, D. Ultrason. Sonochem.2012, 19, 264. (d) He, J.; Ouyang, G.; Yuan, Z.; Tong, R.; Shi, J.; Ouyang, L. Molecules2013, 18, 5142. (e) Bakthadoss, M.; Kannan, D.; Sivakumar, G. Synthesis2012, 793. (f) Shvets, A. A.; Nelyubina, Yu. V.; Lyssenko, K. A.; Kurbatov, S. V. Russ. Chem. Bull., Int. Ed.2012, 61, 1659. [Izv. Akad. Nauk, Ser. Khim.2012, 1642.]

  34. Barman, P. D.; Goyal, D.; Daravath, U. K.; Sanyal, I.; Mandal, S. B.; Banerjee, A. K. Tetrahedron Lett.2013, 54, 3801.

    Article  CAS  Google Scholar 

  35. Rajesh, R.; Raghunathan, R. Tetrahedron Lett. 2010, 51, 5845.

  36. (a) Revathy, K.; Lalitha, A. RSC Adv.2014, 4, 279. (b) Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. J. Med. Chem.2008, 51, 5731. (c) Lotfy, G.; Said, M. M.; El Ashry, El Sayed H.; El Tamany, El Sayed H.; Al-Dhfyan, A.; Abdel Aziz, Y. M.; Barakat, A. Bioorg. Med. Chem.2017, 25, 1514. (d) Jayashankaran, J.; Manian, R. D. R. S.; Venkatesan, R.; Raghunathan, R. Tetrahedron2005, 61, 5595. (e) Sridhar, G.; Raghunathan, R. Synth. Commun.2006, 36, 21.

  37. Dhanalakshmi, P.; Babu, S. S.; Thimmarayaperumal, S.; Shanmugam, S. RSC Adv.2015, 5, 33705.

    Article  CAS  Google Scholar 

  38. Li, X.; Zheng, A.; Liu, B.; Yu, X.; Yi, P. J. Heterocycl. Chem.2010, 47, 1157.

    Article  CAS  Google Scholar 

  39. (a) Maheswari, S. U.; Balamurugan, K.; Perumal, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett.2010, 20, 7278. (b) Suresh Babu, A.; Raghunathan, R. Tetrahedron2007, 63, 8010. (c) Hussein, E. M.; Abdel-Monem, M. I. ARKIVOC2011, (x), 85. (d) Hussein, E. M.; Ahmed, S. A.; El Guesmi, N.; Khairou, K. S. J. Chem. Res.2017, 41, 346. (e) Babu, A. R. S.; Raghunathan, R.; Gayatri, G.; Sastry, G. N. J. Heterocycl. Chem.2006, 43, 1467. (f) Huang, Z.; Zhao, Q.; Chen, G.; Wang, H.; Lin, W.; Xu, L.; Liu, H.; Wang, J.; Shi, D.; Wang, Y. Molecules2012, 17, 12704. (g) Dandia, A.; Jain, A. K.; Laxkar, A. K.; Bhati, D. S. Tetrahedron Lett.2013, 54, 3180. (h) Vidya, S.; Priya, K.; Velayudhan Jayasree, D.; Deepthi, A.; Biju, P. G. Synth. Commun.2019, 49, 1592.

  40. (a) Nallamala, S.; Raghunathan, R. Int. J. Carbohydr. Chem.2013, 1. (b) Nallamala, S.; Raghunathan, R. Int. J. Chem. Pharm. Sci.2013, 4, 117.

  41. (a) Arun, Y.; Saranraj, K.; Balachandran, C.; Perumal, P. T. Eur. J. Med. Chem.2014, 74, 50. (b) Dandia, A.; Jain, A. K.; Laxkar, A. K.; Bhati, D. S. Tetrahedron Lett.2013, 54, 3180. (c) Vidya, S.; Priya, K.; Velayudhan Jayasree, D.; Deepthi, A.; Biju, P. G. Synth. Commun.2019, 49, 1592.

  42. (a) Dandia, A.; Jain, A. K.; Bhati, D. S. Tetrahedron Lett.2011, 52, 5333. (b) Lakshmi, N. V.; Thirumurugan, P.; Perumal, P. T. Tetrahedron Lett.2010, 51, 1064. (c) Liu, H.; Dou, G.; Shi, D. J. Comb. Chem.2010, 12, 292. (d) Dandia, A.; Jain, A. K.; Laxkar, A. K.; Bhati, D. S. Tetrahedron2013, 69, 2062.

Download references

The study was supported by the Russian Foundation for Basic Research (project No. 18-33-01035).

Author information

Authors and Affiliations

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

    Alexei N. Izmest’ev, Galina А. Gazieva & Angelina N. Kravchenko

  2. Plekhanov Russian University of Economics, 36 Stremyannyy Pereulok, Moscow, 117997, Russia

    Angelina N. Kravchenko

Authors
  1. Alexei N. Izmest’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Galina А. Gazieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Angelina N. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alexei N. Izmest’ev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 255–264

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Izmest’ev, A.N., Gazieva, G.А. & Kravchenko, A.N. Regioselectivity of (3+2) cycloaddition of azomethine ylides to activated olefins in the synthesis of spiro[oxindole-3,2′-pyrrolidine] derivatives. Chem Heterocycl Comp 56, 255–264 (2020). https://doi.org/10.1007/s10593-020-02654-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02654-z

Keywords

Search

Navigation