A Simple and One-Pot Synthesis of β-Sultams by Using the Vilsmeier Reagent
Maaroof Zarei
Department of Chemistry, College of Sciences, Hormozgan University, Bandar Abbas, 71961 Iran
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Aliasghar Jarrahpour
Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454 Iran
E-mail: [email protected]Search for more papers by this authorMaaroof Zarei
Department of Chemistry, College of Sciences, Hormozgan University, Bandar Abbas, 71961 Iran
Search for more papers by this authorCorresponding Author
Aliasghar Jarrahpour
Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454 Iran
E-mail: [email protected]Search for more papers by this authorAbstract
Mild and efficient one-pot synthesis of β-sultams with the Vilsmeier reagent proceeded in good to excellent yield. [2 + 2] Cycloaddition of imines with sulfenes (prepared in situ) afforded the corresponding cis-β-sultams. Optimization of solvents, molar ratio of reagents,and temperature was performed. Toxic and corrosive compounds have been avoided in this novel method.
REFERENCES AND NOTES
- 1For a review, see: Hansch, C.; Sammes, P. G.; Taylor, J. B. Comprehensive Medicinal Chemistry; Pergamon Press: Oxford, 1990; Vol. 2, Chapter 7.1.
- 2(a) Long, T. E.; Turos, E. Curr Med Chem Anti-Infective Agents 2002, 1, 251; (b) Southgate, R. Contemp Org Synth 1994, 1, 417; (c) Morin, R. B.; Gorman, M. Chemistry and Biology of β-Lactam Antibiotics; Academic Press: New York, 1982; (d) Georg, G. I. The Organic Chemistry of β-Lactams; Verlag Chemie: New York, 1993; (e) J. R. Hwu, S. K. Ethiraj, G. H. Hakimelahi, Mini Rev Med Chem 2003, 3, 305; (f) Meshram, J.; Ali, P.; Tiwari, V. J Het Chem 2010, 47, 1454; (g) Keri, R. S.; Hosamani, K. M.; Shingalapur, R. V.; Reddy, H. R. S. Eur J Med Chem 2009, 44, 5123.
- 3
Kalir, A.;
Kalir, H. H. Biological activity of sulfonic acid derivatives. In The Chemistry of Sulfonic Acids, Esters and Their Derivatives; S. Patai; Z. Rappoport Eds.; Interscience Publication, Wiley: Chichester, 1991; 767–787.
10.1002/0470034394.ch18 Google Scholar
- 4 Baxter, N. J.; Rigoreau, L. J. M.; Laws, A. P.; Page, M. I. J Am Chem Soc 2000, 122, 3375.
- 5 Baxter, N. J.; Laws, A. P.; Rigoreau, L. J. M.; Page, M. I. J Chem Soc, Perkin Trans 2 1996, 2245.
- 6(a) Iwama, T.; Kataoka, T.; Muraoka, O.; Tanabe, G. Tetrahedron 1998, 54, 5507; (b) Koller, W.; Linkies, A.; Rehling, H.; Reuschling, D. Tetrahedron Lett 1983, 24, 2131.
- 7 Iwama, T.; Kataoka, T.; Muraoka, O.; Tanabe, G. J Org Chem 1998, 63, 8355.
- 8(a) Hinchliffe, P. S.; Wood, J. M.; Davis, A. M.; Austin, R. P.; Beckett, P. R.; Page, M. I. Org Biomol Chem 2003, 1, 67; (b) Page, M. I. Acc Chem Res 2004, 37, 297; (c) Tsang, W. Y.; Ahmed, N.; Harding, L. P.; Hemming, K.; Laws, A. P.; Page, M. I. J Am Chem Soc 2005, 127, 8946.
- 9 Page, M. I.; Hinchliffe, P. S.; Wood, J. M.; Harding, L. P.; Laws, A. P. Bioorg Med Chem Lett 2003, 13, 4489.
- 10 Llinás, A.; Ahmed, N.; Cordaro, M.; Laws, A. P.; Frère, J.-M.; Delmarcelle, M.; Silvaggi, N. R.; Kelly, J. A.; Page, M. I. Biochemistry 2005, 44, 7738.
- 11 Ward, R. J.; Lallemand, F.; Witte, P.; Crichton, R. R.; Piette, J.; Tipton, K.; Hemmings, K.; Pitard, A.; Page, M.; Della Corte, L.; Taylor, D.; Dexter, D. Biochem Pharmacol 2011, 81, 743.
- 12(a) Iwama, T.; Ogawa, M.; Kataoka, T.; Muraoka, O.; Tanabe, G. Tetrahedron 1998, 54, 8941; (b) Grunder, E.; Leclerc, G. Synthesis 1989, 135; (c) Enders, D.; Moll, A. Synthesis 2005, 1807.
- 13(a) Zajac, M.; Peters, R. Chem Eur J 2009, 15, 8204; (b) For review: Iwama, T.; Kataoka, T. Rev Bras Mandioca Rev Heteroatom Chem 1996, 15, 25.
- 14(a) Enders, D.; Wallert, S.; Runsink, J. Synthesis 2003, 1856; (b) Enders, D.; Moll, A.; Schaadt, A.; Runsink, J.; Raabe, G. Eur J Org Chem 2003, 3923; (c) Velazquez, F.; Arasappan, A.; Chen, K.; Sannigrahi, M.; Venkatraman, S.; McPhail, A. T.; Chan, T.-M.; Shih, N.-Y.; Njoroge, F. G. Org Lett 2006, 8, 789.
- 15 Baldoli, C.; Del Buttero, P.; Perdicchia, D.; Pilati, T. Tetrahedron 1999, 55, 14089.
- 16 Barton, W. R. S.; Paquette, L. A. Can J Chem 2004, 82, 113.
- 17(a) Burgess, E. M.; Williams, W. M. J Am Chem Soc 1972, 94, 4386; (b) Atkins, G. M. Jr.; Burgess, E. M. J Am Chem Soc 1967, 89, 2502.
- 18 Lewis, A. K. de K; Mok, B. J.; Tocher, D. A.; Wilden, J. D.; Caddick, S. Org Lett 2006, 8, 5513.
- 19(a) Tsuge, O.; Iwanami, S. Bull Chem Soc Jpn 1970, 43, 3543; (b) Hiraoka, T.; Kobayashi, T. Bull Chem Soc Jpn 1975, 48, 480; (c) Szymonifka, M. J.; Heck, J. V. Tetrahedron Lett 1989, 30, 2869; (d) Gordeev, M. F.; Gordon, E. M.; Patel, D. V. J Org Chem 1997, 62, 8177.
- 20 Zajac, M.; Peters, R. Org Lett 2007, 9, 2007.
- 21For review see (a) King, J. F. Acc Chem Res 1975, 8, 10; (b) Zwanenburg, B. Sci Synth 2004, 27, 123; (c) Optiz, G. Angew Chem Int Ed 1967, 6, 107.
- 22(a)
Shirota, Y.;
Nagai, T.;
Tokura, N. Bull Chem Soc Jpn 1966, 39, 405;
(b)
Shirota, Y.;
Nagai, T.;
Tokura, N. Tetrahedron 1967, 23, 639;
(c)
Shirota, Y.;
Nagai, T.;
Tokura, N. Tetrahedron Lett 1968, 9, 2343;
10.1016/S0040-4039(00)61990-1 Google Scholar(d) Shirota, Y.; Nagai, T.; Tokura, N. Tetrahedron 1969, 25, 3193; (e) Nagai, T.; Tokura, N. Int J Sulfur Chem 1972, 7B, 207.
- 23(a) Hesse, G. Reichold, E. Chem Ber 1957, 90, 2101; (b) Hesse, G.; Reichold, E.; Majmudar, S. Chem Ber 1957, 90, 2106; (c) Hesse, G.; Majmudar, S. Chem Ber 1960, 93, 1129; (d) Fischer, N. H. Synthesis 1970, 393.
- 24(a)
Charlton, J. L.;
de Mayo, P. Can J Chem 1968, 46, 55;
(b)
Weintraub, S. T.;
Plummer, B. F. J Org Chem 1971, 36, 361;
(c)
Durst, T.;
King, J. F. Can J Chem 1966, 44, 1869;
(d)
Langendries, R. F. T.;
De Schryver, F. C. Tetrahedron Lett 1972, 13, 4781;
10.1016/S0040-4039(01)94426-0 Google Scholar(e) King, J. F.; Harding, D. R. K. Chem Commun 1971, 959.
- 25(a)
Lwowski, W.;
Scheiffele, E. J Am Chem Soc 1965, 87, 4359;
(b)
Van Leusen, A. M.;
Mulder, R. J.;
Strafing, J. Tetrahedron Lett 1964, 5, 543.
10.1016/S0040-4039(00)90367-8 Google Scholar
- 26(a) Jarrahpour, A.; Zarei, M. Tetrahedron Lett 2009, 50, 1568; (b) Jarrahpour, A.; Zarei, M. Tetrahedron 2010, 66, 5017.
- 27 Rai, A.; Rai, V. K.; Singh, A. K.; Yadav, L. D. S. Eur J Org Chem 2011, 4804302.
- 28(a) Jarrahpour, A.; Zarei, M. Tetrahedron Lett 2007, 48, 8712; (b) Jarrahpour, A.; Zarei, M. Tetrahedron 2009, 65, 2927; (c) Jarrahpour, A.; Fadavi, A.; Zarei, M. Bull Chem Soc Jpn 2011, 84, 320; (d) Zarei, M.; Mohamadzadeh, M. Tetrahedron 2011, 67, 5832.
- 29 CAS No. 3724-43-4. For example Acros product No. 29577 or Aldrich product no. 280909.