Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 17
Submit an article Journal homepage
379
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Efficient synthesis of N-nosyl-protected 3-azabicyclo[4.3.0]nonen-8-one by an aniline- and nitrobenzene-mediated Pauson–Khand cyclization

Kyosuke KanedaMedicinal Chemistry Department, Hokkaido Pharmaceutical University School of Pharmacy, Sapporo, Hokkaido, JapanCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0003-2415-2685
ORCID Icon,
Ryuki TairaMedicinal Chemistry Department, Hokkaido Pharmaceutical University School of Pharmacy, Sapporo, Hokkaido, Japan
&
Tsubasa FukuzawaMedicinal Chemistry Department, Hokkaido Pharmaceutical University School of Pharmacy, Sapporo, Hokkaido, Japan
Pages 1622-1629 | Received 09 Apr 2017, Published online: 06 Jul 2017

References

  • Kobayashi, J.; Watanabe, D.; Kawasaki, N.; Tsuda, M. J. Org. Chem. 1997, 62, 9236–9239.
  • Chi, Y.; Yan, W.-M.; Li, J.-S. Phytochemistry 1990, 29, 2376–2378.
  • Djerassi, C.; Kutney, J. P.; Shamma, M. Tetrahedron 1962, 18, 183–188.
  • Hammouda, Y.; Motawi, M. M. Egypt Pharm. Bull. 1959, 41, 73–79.
  • (a) Clark, J. S.; Xu, C. Angew. Chem. Int. Ed. 2016, 55, 4332–4335; (b) Honda, T.; Kaneda, K. J. Org. Chem. 2007, 72, 6541–6547; (c) Kaneda, K.; Honda, T. Tetrahedron 2008, 64, 11589–11593; (d) Ockey, D. A.; Lewis, M. A.; Schore, N. E. Tetrahedron 2003, 59, 5377–5381; and also see (e) Sezer, S.; Gümrükçü, Y.; Bakırcı, İ.; Ünver, M. Y.; Tanyeli, C. Tetrahedron: Asymmetry 2012, 23, 662–669; (f) Kavanagh, Y.; O’Brien, M.; Evans, P. Tetrahedron 2009, 65, 8259–8268; (g) Bolton, G. L. Tetrahedron Lett. 1996, 37, 3433–3436.
  • (a) Torres, R. R., Ed.; The Pauson–Khand Reaction: Scope, Variations and Applications; John Wiley & Sons Ltd: New York, 2012; (b) Lee, H.-W.; Kwong, F.-Y. Eur. J. Org. Chem. 2010, 789–811; (c) Blanco-Urgoiti, J.; Añorbe, L.; Pérez-Serrano, L.; Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2004, 33, 32–42; (d) Schore, N. E. Org. React. 1991, 40, 1–90; (e) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977–981.
  • Wuts, P. G.; Greene, T. W. Greene’s Protective Groups in Organic Synthesis; John Wiley & Sons, New York, 2006.
  • Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373–6374.
  • (a) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem. Int. Ed. 1997, 36, 2801–2804; (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. J. Syn. Org. Chem. Jpn. 1999, 57, 158–169.
  • (a) Yang, K.; Ke, M.; Lin, Y.; Song, Q. Green Chem. 2015, 17, 1395–1399; (b) Mertens, M. D.; Hinz, S.; Müller, C. E.; Gütschow, M. Bio. Med. Chem. 2014, 22, 1916–1928; (c) He, H.; Feng, J.; He, J.; Xia, Q.; Ren, Y.; Wang, F.; Feng, L. RSC Adv. 2016, 6, 4310–4320; (d) Kraljević, T. G.; Harej, A.; Sedić, M.; Pavelić, S. K.; Stepanić, V.; Drenjančević, D.; Raić-Malić, S. Eur. J. Med. Chem. 2016, 124, 794–808; (e) Pardeshi, K. A.; Malwal, S. R.; Banerjee, A.; Lahiri, S.; Rangarajan, R.; Chakrapani, H. Bio. Med. Chem. Lett. 2015, 25, 2694–2697.
  • (a) Mitsunobu, O. Synthesis 1981, 1, 1–28; (b) Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709–5712.
  • Sugimura, T.; Hagiya, K. Chem. Lett. 2007, 36, 566–567.
  • Ramadas, K.; Srinivasan, N. Synth. Commun. 1992, 22, 3189–3195.
  • Lee, H-Y.; An, M. Bull. Korean Chem. Soc. 2004, 25, 1717–1719.

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:

Order Reprints Request Corporate Permissions

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:

Request Academic Permissions

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.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.