Highly stereoselective β-lactam synthesis via the Staudinger reaction using poly aromatic imines

Heterocyclic Communications

Volumn 15, Issue 3, 2009, Pages 229-232

  Bandyopadhyay, Debasish ^a   Xavier, Monica ^a   Banik, Bimal K ^a  

^a UNIVERSITY OF TEXAS PAN AMERICAN   (United States)

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Indexed keywords

EID: 74549207556     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2009.15.3.229     Document Type: Article

References (16)

1. For example, (a) A. K. Bose, M. S. Manhas, B. K. Banik and V. Srirajan, In The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Material Science; Greenberg, A.; Breneman, C. M.; Liebman, J. F. Eds; Wiley-Interscience: New York, 2000;157-214 Chapter 7 (β-Lactams: Cyclic Amides of Distinction.).
2. M. Suffness In Taxol Science and Applications, CRC Press; Boca Raton, FL 1995.
3. (a) S. K. Dasgupta and B. K. Banik, Tetrahedron Lett., 43, 9445, (2002).
4. (b) B. K. Banik, S. Samajdar and I. Banik, Tetrahedron Lett, 44, 1699 (2003).
5. (c) B. K. Banik, I. Banik and L. Hackfeld, L Heterocycles, 59, 505 (2003).
6. (a) I. Banik, F. F. Becker and B. K. Banik, B. K., J. Med. Chem., 46, 12 (2003).
7. (b) B. K. Banik, F. F. Becker and I. Banik, Bioorg. Med. Chem, 12, 2523 (2004).
8. (c) B. K. Banik, I. Banik, I. And F. F. Becker, Bioorg. Med. Chem., 13, 3611 (2004).
9. G. I. Georg and V. T. Ravikumar, In The Organic Chemistry of β-Lactams; VCH publishers; Ed. Georg, G. I. New York, 1992.
10. A. K. Bose, B. Lal, B. Dayal and M. S. Manhas, Tetrahedron Lett., 30, 2633 (1974).
11. B. K. Banik, B. Lecea, A. Arrieta, A. Cozar and F. P. Cossio, Anew. Chem., 46, 3028 (2007). Also, see ref 4.
12. For the preparation of trans β-lactams, see: (a) B. Alcaide and A. Vicente-Rodriguez, Tetrahedron Lett., 40, 2005 (1999).
13. (b) A. Afonso, S. B. Rosenblum, M. S. Puar and A. T. McPhail, Tetrahedron Lett., 39, 7431 (1998).
14. (c) M. Endo and R. Droghini, Bioorg. & Med. Chem. Lett., 3, 2483 (1993).
15. (d) A. K. Bose, B. K. Banik, B. K and M. S. Manhas, Tetrahedron Lett., 36, 213 (1995).
16. A representative experiment procedure is given below. A solution consisting of phthalimidoacetic acid (1.5 mmol) in dichloromethane (10 mL) was added 2-iodo-N-methylpyridine (2 mmol) and triethylamine (6 mmol) at icecold temperature. This mixture was stirred for 1h. Imine (1 mmol) in dry dichloromethane (10 mL) was then to it at 0°C. The reaction mixture was then stirred overnight at room temperature, washed with saturated sodium bicarbonate solution (10 mL), dilute hydrochloric acid (10%, 10 mL), brine (10 mL), dried with anhydrous sodium sulfate and evaporated to obtain the crude product. Proton NMR indicated the presence of trans was ∼-lactams only. The pure product was then isolated via column chromatography over silica gel using ethyl acetate-hexanes (1:4) as the solvent. All the compounds have been characterized by IR, NMR and MS analyses.