Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 7
390
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Lewis acid catalyzed Povarov reaction of pentafulvenes and spiro[2,4]-hepta-[4,6]-diene: An efficient access to cyclopentene fused quinolines

, , &
Pages 816-829 | Received 20 Dec 2017, Published online: 06 Mar 2018

References

  • (a) Kumar, A.; Srivastava, S.; Gupta, G.; Chaturvedi, V.; Sinha, S.; Srivastava, R. ACS Comb. Sci. 2011, 13, 65–71. (b) Kishore, N.; Mishra, B. B.; Tripathi, V.; Tiwari, V. K. Fitoterapia 2009, 80, 149–163. (c) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913–2916. (d) Carling, R. W.; Lesson, P. D.; Moseley, A. M.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshal, G. R. J. Med. Chem. 1992, 35, 1942–1953. (e) Carling, R. W.; Lesson, P. D.; Moseley, A. M.; Smith, J. D.; Saywell, K.; Trickelbank, M. D.; Kemp, J. A.; Marshal, G. R.; Foster, A. C.; Grimwood, S. Bioorg. Med. Chem. Lett. 1993, 3, 65–70. (f) Paris, D.; Cottin, M.; Demonchaux, P.; Augert, G.; Dupassieux, P.; Lenoir, P.; Peck, M. J.; Jasserand, D. J. Med. Chem. 1995, 38, 669–685.
  • (a) Suresh, R.; Muthusubramanian, S.; Senthilkumaran, R.; Manickam, G. J. Org. Chem. 2012, 77, 1468–1476. For reviews, see: (b) Michael, J. P. Nat. Prod. Rep. 1997, 14, 605–618. (c) Bray, P. G.; Ward, S. A.; O’Neil, P. M. Curr. Top. Microbiol. Immunol. 2005, 295, 3–38. (d) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627–646. (e) Gasparotto, V.; Castagliuolo, I.; Chiarelotto, G.; Pezzi, V.; Montanaro, D. P.; Brun, D.; Palù, G.; Viola, G.; Ferlin, M. G. J. Med. Chem. 2006, 49, 1910–1915. (f) Jain, S.; Chandra, V.; Jain, P. K.; Pathak, K.; Pathak, D.; Vaidya, A. Arab. J. Chem. 2016, in press. DOI: 10.1016/j.arabjc.2016.10.009.
  • (a) Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1963, 2, 953–956. (b) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1963, 3, 2039–2041. (c) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656–670.
  • (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 9, 1195–1202. (b) Kobayashi, S.; Komlyama, S.; Ishitani, H. Biotechnol. Bioeng. 1998, 1, 23–31. For recent reviews, see: (c) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721–2750. (d) Fochi, M.; Caruana, L.; Bernardi, L. Synthesis 2014, 46, 135–157.
  • (a) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913–2916. (b) Burai, R.; Ramesh, C.; Shorty, M.; Curpan, R.; Bologa, C.; Sklar, L. A.; Oprea, T.; Prossnitzd, R.; Arterburn, J. B. Org. Biomol. Chem. 2010, 8, 2252–2259.
  • (a) Thiele, J. Ber. Dtsch. Chem. Ges. 1900, 33, 666. (b) Thiele, J.; Balhorn, H. Liebigs Ann. Chem. 1906, 348, 1–15.
  • Preethalayam, P.; Krishnan, K. S.; Thulasi, S.; Chand, S. S.; Joseph, J.; Nair, V.; Jaroschik, F.; Radhakrishnan, K. V. Chem. Rev. 2017, 117, 3930–3989.
  • (a) Rawson, D. I.; Carpenter, B. K.; Hoffmann, H. M. R. J. Am. Chem. Soc. 1979, 101, 1786–1793. (b) Noyori, R.; Hayakawa, Y.; Takaya, H.; Murai, S.; Kobayashi, R.; Sonoda, N. J. Am. Chem. Soc. 1978, 100, 1759–1765.
  • (a) Imafuku, K.; Arai, K. Synthesis 1989, 1989, 501. (b) Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201–205.
  • (a) Harre, M.; Raddatz, P.; Walenta, R.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 480. (b) Gleiter, R.; Borzyk, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 1001–1003.
  • (a) Himeda, Y.; Yamataka, H.; Ueda, I.; Hatanaka, M. J. Org. Chem. 1997, 62, 6529–6538. (b) Nair, V.; Nair, A. G.; Radhakrishnan, K. V.; Nandakumar, M. V.; Rath, N. P. Synlett. 1997, 12, 767–768.
  • (a) Gupta, Y. N.; Doa, M. J.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7336–7338. (b) Yoshida, Z.-I.; Shibata, M.; Ogino, E.; Sugimoto, T. Angew. Chem., Int. Ed. Engl. 1985, 24, 60–61. (c) Houk, K. N.; Luskus, L. J.; Bhacca, N. S. J. Am. Chem. Soc. 1970, 92, 6392–6394.
  • (a) Suda, M.; Hafner, K. Tetrahedron Lett. 1977, 18, 2453–2456. (b) Wu, T. C.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 5308–5309. (c) Hong, B.-C.; Shr, Y. J.; Wu, J.-L.; Gupta, A. K.; Lin, K.-J. Org. Lett. 2002, 4, 2249–2252.
  • (a) Sakai, K.; Kobori, T.; Fujisawa, T. Tetrahedron Lett. 1981, 22, 115–118. (b) Buchi, G.; Decorzant, D. B. R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208–3209. (c) Wang, Y.; Mukherjee, D.; Birney, D.; Houk, K. N. J. Org. Chem. 1990, 55, 4504–4506. (d) Hudlicky, T.; Kutchan, T. M.; Wilson, S. R.; Mao, D. T. J. Am. Chem. Soc. 1980, 102, 6351–6353. (e) Antczak, K.; Kingston, J. F.; Fallis, A. G. Can. J. Chem. 1984, 62, 2451–2455. (f) Brayer, J.-L.; Alazard, J.-P.; Thal, C. J. Chem. Soc. Chem. Commun. 1983, 257–258.
  • (a) Radhakrishnan, K. V.; Krishnan, K. S.; Bhadbhade, M. M.; Bhosekar, G. V. Tetrahedron Lett. 2005, 46, 4785–4788. (b) Krishnan, K. S.; Sajisha, V. S.; Anas, S.; Suresh, C. H.; Bhadbhade, M. M.; Bhosekar, G. V.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 5952–5961. (c) Krishnan, K. S.; Suresh, E.; Mathew, S.; Radhakrishnan, K. V. Synthesis 2006, 11, 1811–1818. (d) Krishnan, K. S.; Smitha, M.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 12345–12350. (e) Kuthanapillil, J. M.; Thulasi, S.; Rajan, R.; Krishnan, K. S.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2011, 67, 1272–1280.
  • (a) Anas, S.; Sajisha, V. S.; Mohanlal, S.; Radhakrishnan, K. V. Synlett. 2006, 15, 2399–2402. (b) Anas, S.; John, J.; Sajisha, V. S.; Rajan, R.; Suresh, E.; Radhakrishnan, K. V. Org. Biomol. Chem. 2007, 5, 4010–4019. (c) Anas, S.; Sajisha, V. S.; John, J.; Joseph, N.; George, S. C.; Radhakrishnan, K. V. Tetrahedron 2008, 64, 9689–9697. (d) Sajisha, V. S.; Anas, S.; John, J.; Radhakrishnan, K. V. Synlett. 2009, 18, 2885–2895. (e) Rajan, R.; John, J.; Thulasi, S.; Radhakrishnan, K. V.; Sawant, R. C. Synthesis 2010, 21, 3649–3655. (f) George, S. C.; Thulasi, S.; Anas, S.; Radhakrishnan, K. V.; Yamamoto, Y. Org. Lett. 2011, 13, 4984–4987. (g) Joseph, N.; Rajan, R.; John, J.; Devika, N. V.; Chand, S. S.; Suresh, E.; Pihko, P. M.; Radhakrishnan, K. V. RSC Adv. 2013, 3, 7751–7757. (h) Chand, S. S.; Jijy, E.; Prakash, P.; Szymoniak, J.; Preethanuj, P.; Dhanya, B. P.; Radhakrishnan, K. V. Org. Lett. 2013, 15, 3338–3341. (i) John, J.; Rajan, R.; Chand, S. S.; Prakash, P.; Joseph, N.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2013, 69, 152–159. (j) Chand, S. S.; Saranya, S.; Preethanuj, P.; Dhanya, B. P.; Jijy, E.; Prakash, P.; Sasidhar, B. S.; Szymoniak, J.; Santhini, P. V.; Radhakrishnan, K. V. Org. Biomol. Chem. 2014, 12, 3045–3061. (k) Prakash, P.; Aparna, P. S.; Jijy, E.; Santhini, P. V.; Varughese, S.; Radhakrishnan, K. V. Synlett. 2014, 25, 275–279. (l) Prakash, P.; Jijy, E.; Aparna, P. S.; Viji, S.; Radhakrishnan, K. V. Tetrahedron Lett. 2014, 55, 916–920. (m) Chand, S. S.; Sasidhar, B. S.; Prakash, P.; Sasikumar, P.; Preethanuj, P.; Jaroschik, F.; Harakat, D.; Vasse, J.-L.; Radhakrishnan, K. V. RSC Adv. 2015, 5, 38075–38084. (n) Chand, S. S.; Gopalan, G.; Santhini, P. V.; Preethanuj, P.; John, J.; Harakat, D.; Jaroschik, F.; Radhakrishnan, K. V. Org. Lett. 2016, 18, 964–967. (o) Vijayan, A.; Baiju, T. V.; Varughese, S.; Radhakrishnan, K. V. Tetrahedron Lett. 2016, 57, 2965–2968. (p) Preethanuj, P.; Jijitha, V.; Vijayan, A.; John, J.; Radhakrishnan, K. V. Synthesis 2017, 49, 1816–1833. (q) Santhini, P. V.; Chand, S. S.; John, J.; Varma, R. L.; Jaroschik, F.; Radhakrishnan, K. V. Synlett. 2017, 28, 951–956.
  • (a) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357–7360. (b) Glushkov, V. A.; Tolstikov, A. G. Russ. Chem. Rev. 2008, 77, 137–159. (c) Kulkarni, A. R.; Thakur, G. A. Tetrahedron Lett. 2013, 54, 6592–6595. (d) Odinokov, V. N.; Tolstikov, A. G.; Savchenko, R. G.; Lukina, E. S.; Afon´kina, S. R.; Nedopekin, D. V.; Khalilov, L. M. Russ. Chem. Bull. Int. Ed. 2013, 62, 2377–2384.
  • Stepakov, A. V.; Boitsov, V. M.; Larina, A. G.; Molchanov, A. P. Russ. J. Org. Chem. 2014, 50, 1070–1080.
  • Bologa, C. G.; Revankar, C. M.; Young, S. M.; Edwards, B. S.; Arterburn, J. B.; Kiselyov, A. S.; Parker, M. A.; Tkachenko, S. E.; Savchuck, N. P.; Sklar, L. A.; Nat. Chem. Biol. 2006, 2, 207–212.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.