Skip to main content
Log in

A facile approach to α,β-unsaturated lactams by ring-closing metathesis

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A facile and efficient strategy for the synthesis of α,β-unsaturated lactams through ring-closing metathesis of easily prepared diene amides is being reported here. Reaction conditions were optimized for metathetic cyclization of diene amides to obtain five- to sevenmembered unsubstituted and β-substituted α,β-unsaturated lactams in good to excellent yield.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1

Similar content being viewed by others

References

  1. (a) Grohmann, M.; Buck, S.; Schäffler, L.; Maas, G. Adv. Synth. Catal. 2006, 348, 2203. (b) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. (Tokyo) 1991, 44, 113. (c) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge K., Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. (Tokyo) 1991, 44, 117. (d) Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355. (e) Barrett, A. G. M.; Head, J.; Smith, M. L.; Stock, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005. (f) Sherrill, R. G.; Webster Andrews, C.; Bock, W. J.; Davis-Ward, R. G.; Furfine, E. S.; Hazen, R. J.; Rutkowske, R. D.; Spaltenstein, A.; Wright, L. L. Bioorg. Med. Chem. Lett. 2005, 15, 81. (g) Kazmierski, W. M.; Andrews, W.; Furfine, E.; Spaltenstein, A.; Wright, L. Bioorg. Med. Chem. Lett. 2004, 14, 5689. (h) Kazmierski, W. M.; Furfine, E.; Gray-Nunez, Y.; Spaltenstein, A.; Wright, L. Bioorg. Med. Chem. Lett. 2004, 14, 5685. (i) Spaltenstein, A.; Almond, M. R.; Bock, W. J.; Cleary, D. G.; Furfine, E. S.; Hazen, R. J.; Kazmierski, W. M.; Salituro, F. G.; Tung, R. D.; Wright, L. L. Bioorg. Med. Chem. Lett. 2000, 10, 1159.

  2. (a) Ma, D.; Ma, J.; Ding, W.; Dai, L. Tetrahedron: Asymmetry 1996, 7, 2365. (b) Jouin, P.; Castro, B.; Nisato D. J. Chem. Soc., Perkin Trans. 1 1987, 1177. (c) Casiraghi, G.; Spanu, P.; Rassu, G.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1994, 59, 2906. (d) Shiraki, R.; Sumino, A.; Tadano, K.-i.; Ogawa, S. J. Org. Chem. 1996, 61, 2845. (e) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Fujii, Y.; Kizu, H.; Boyd, M. R.; Boettner, F. E.; Doubek, D. L.; Schmidt, J. M.; Chapuis, J.-C.; Michel, C. Tetrahedron 1993, 49, 9151. (f) Koehn, F. E.; Longley, R. E.; Reed, J. K. J. Nat. Prod. 1992, 55, 613. (g) Fuji, K.; Yamada, T.; Fujita, E.; Murata, H. Chem. Pharm. Bull. 1978, 26, 2515. (h) Bosch, J.; Roca, T.; Catena, J.-L.; Llorens, O.; Pérez, J.-J.; Lagunas, C.; Fernández, A. G.; Miquel, I.; Fernández-Serrat, A.; Farrerons, C. Bioorg. Med. Chem. Lett. 2000, 10, 1745. (i) Smith III, A. B.; Hirschmann, R.; Pasternak, A.; Guzman, M. C.; Yokoyama, A.; Sprengeler, P. A.; Darke, P. L.; Emini, E. A.; Schleif, W. A. J. Am. Chem. Soc. 1995, 117, 11113. (j) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101. (k) Moreno-Mañas, M.; Pleixats, R.; Santamaria, A. Synlett 2001, 1784. (l) Rosillo, M.; Casarrubios, L.; Domı́nguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2001, 42, 7029. (m) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 54, 10227.

  3. (a) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1985, Vol. 3, Chap. 1, p. 1. (b) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993, Vol. 44, Chap. 3, p. 189. (c) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996, Vol. 10, Chap. 2, p. 155.

  4. (a) Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276. (b) Ishibashi, H.; Kameoka, C.; Kodama, K.; Sato, T.; Ikeda, M. Tetrahedron, 1996, 52, 489. (c) Baillargeon, P.; Bernard, S.; Gauthier, D.; Skouta, R.; Dory, Y. L. Chem.–Eur. J. 2007, 13, 9223. (d) Kang, S.-K.; Kim, K.-J.; Yu, C.-M.; Hwang, J.-W.; Do, Y.-K. Angew. Chem., Int. Ed. 1997, 36, 5.

  5. (a) Franco Bella, A.; Jackson, L. V.; Walton, J. C. Org. Biomol. Chem. 2004, 2, 421. (b) Andrukiewicz, R.; Loska, R.; Prisyahnyuk, V.; Staliński, K. J. Org. Chem. 2003, 68, 1552. (c) Zoretic, P. A.; Soja, P. J. Org. Chem. 1976, 41, 3587. (d) Baker, J. T.; Sifniades, S. J. Org. Chem. 1979, 44, 2798. (e) Macdonald, S. J. F.; Inglis, G. G. A.; Bentley, D.; Dowle, M. D. Tetrahedron Lett. 2002, 43, 5057. (f) Kawanaka, Y.; Kobayashi, K.; Kusuda, S.; Tatsumi, T.; Murota, M.; Nishiyama, T.; Hisaichi, K.; Fujii, A.; Hirai, K.; Naka, M.; Komeno, M.; Nakai, H.; Toda, M. Bioorg. Med. Chem. Lett. 2002, 12, 2291. (g) Fisyuk, A. S.; Bundel', Yu. G. Chem. Heterocycl. Compd. 1999, 35, 125. [Khim. Geterotsikl. Soedin. 1999, 147.]

  6. (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Coe, S.; Pereira, N.; Geden, J. V.; Clarkson, G. J.; Fox, D. J.; Napier, R. M.; Neve, P.; Shipman, M. Org. Biomol. Chem. 2015, 13, 7655. (d) Fürstner, A.; Langemann, K. Synthesis 1997, 792. (e) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (f) Benedetti, E.; Lomazzi, M.; Tibiletti, F.; Goddard J.-P.; Fensterbank, L.; Malacria, M.; Palmisano, G.; Penoni, A. Synthesis 2012, 44, 3523. (g) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (i) Fürstner, A. Top Catal. 1997, 4, 285. (j) Schuster, M.; Blechert, S. Angew Chem., Int. Ed. Engl. 1997, 36, 2036. (k) Fürstner, A. Top Organomet. Chem. 1998, 1, 37. (l) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization, 2nd ed.; Academic Press; New York, 1997.

  7. (a) Goldring, W. P. D.; Hodder, A. S.; Weiler, L. Tetrahedron Lett. 1998, 39, 4955. (b) Hassan, H. M. A. Chem. Commun. 2010, 46, 9100. (c) Barrett, A. G. M.;Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. Chem. Commun. 1996, 2231. (d) Huang, C.-G.; Chang, B.-R.; Chang, N.-C. Tetrahedron Lett. 2002, 43, 2721. (e) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1. (f) Yang, Q.; Lai, Y.-Y.; Xiao, W.-J.; Alper, H. Tetrahedron Lett. 2008, 49, 7334. (g) Capon, B.; Kwok, F. C. J. Am. Chem. Soc. 1989, 111, 5346. (h) Hermet, J.-P.; Caubert, V.; Langlois, N. Synth. Commun. 2006, 36, 2253.

  8. (a) Chavan, S. P.; Pathak, A. B.; Dhawane, A. N.; Kalkote, U. R. Synth. Commun. 2007, 37, 1503. (b) Chavan, S. P.; Pathak, A. B.; Pawar, K. P. Synthesis 2015, 47, 955.

  9. (a) Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. (b) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 2011, 43, 669. (c) Dumoulin, D.; Lebrun, S.; Deniau, E.; Couture, A.; Grandclaudon, P. Eur. J. Org. Chem. 2009, 22, 3741. (d) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 2012, 44, 1410.

  10. (a) Bordner, J.; Rapoport, H. J. Org. Chem. 1965, 30, 3824. (b) Alves, J. C. F. J. Braz. Chem. Soc. 2007, 18, 4, 855. (c) Fisyuk, A. S.; Poendaev, N. V.; Bundel', Y. G. Mendeleev Commun. 1998, 8, 12.

  11. (a) Hua, D. H.; Zhang, F.; Chen, J.; Robinson, P. D. J. Org. Chem. 1994, 59, 5084. (b) Sundberg, R. J.; Bukowick, P. A.; Holcombe, F. O. J. Org. Chem. 1967, 32, 2938. (c) Boll, P. M.; Hansen, J.; Simonsen, O. Tetrahedron 1984, 40, 171.

  12. Reimschuessel, H. K.; Sibilia, J. P.; Pascale, J. V. J. Org. Chem. 1969, 34, 959.

    Article  CAS  Google Scholar 

  13. Garnier, E. C.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 7449.

    Article  CAS  Google Scholar 

Download references

H. Y. Gondal is thankful to Embassy of France in Pakistan for the financial support for postdoctoral studies at MNHN, Paris, France.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Humaira Yasmeen Gondal.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(3), 183–191

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gondal, H.Y., Buisson, D. A facile approach to α,β-unsaturated lactams by ring-closing metathesis. Chem Heterocycl Comp 52, 183–191 (2016). https://doi.org/10.1007/s10593-016-1858-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1858-y

Keywords

Navigation