Thermally induced isomerization of cis-1,3,4-trisubstituted 2- azetidinones

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4453-4455

  Alcaide, Benito ^a   Almendros, Pedro ^a   Salgado, Nati R ^a   Rodríguez Vicente, Alberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINONE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; ISOMERISM; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

ANTI-BACTERIAL AGENTS; AZETIDINES; ISOMERISM; LACTAMS; THERMODYNAMICS;

EID: 0034647707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000229x     Document Type: Article

References (64)

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38. See, for instance: (a) Alcaide, A.; Almendros, P.; Aragoncillo, A.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (c) Alcaide, B.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (d) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (e) Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015. (f) Alcaide, B.; Almendros, P.; Salgado, N. R. J. Org. Chem. 2000, 65, 3310.
39. See, for instance: (a) Alcaide, A.; Almendros, P.; Aragoncillo, A.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (c) Alcaide, B.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (d) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (e) Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015. (f) Alcaide, B.; Almendros, P.; Salgado, N. R. J. Org. Chem. 2000, 65, 3310.
40. See, for instance: (a) Alcaide, A.; Almendros, P.; Aragoncillo, A.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (c) Alcaide, B.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (d) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (e) Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015. (f) Alcaide, B.; Almendros, P.; Salgado, N. R. J. Org. Chem. 2000, 65, 3310.
41. See, for instance: (a) Alcaide, A.; Almendros, P.; Aragoncillo, A.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (c) Alcaide, B.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (d) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (e) Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015. (f) Alcaide, B.; Almendros, P.; Salgado, N. R. J. Org. Chem. 2000, 65, 3310.
42. See, for instance: (a) Alcaide, A.; Almendros, P.; Aragoncillo, A.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (c) Alcaide, B.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (d) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (e) Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015. (f) Alcaide, B.; Almendros, P.; Salgado, N. R. J. Org. Chem. 2000, 65, 3310.
43. See, for instance: (a) Alcaide, A.; Almendros, P.; Aragoncillo, A.; Salgado, N. R. J. Org. Chem. 1999, 64, 9596. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (c) Alcaide, B.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (d) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (e) Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015. (f) Alcaide, B.; Almendros, P.; Salgado, N. R. J. Org. Chem. 2000, 65, 3310.
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47. For selected recent papers on the synthesis of trans-azetidinones, see: (a) Wu, G.; Wong, Y.; Ding, Z. J. Org. Chem. 1999, 64, 3714. (b) Panunzio, M.; Bacchi, S.; Campana, E.; Fiume, L.; Vicennati, P. Tetrahedron Lett. 1999, 40, 8495. (c) Podlech, J.; Linder, M. R. J. Org. Chem. 1997, 62, 5873. (d) Podlech, J. Synlett. 1996, 582. (d) Browne, M.; Burnett, D. A.; Caplen, M. A.; Chen, L.-Y.; Clader, J. W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Viziano, M.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555.
48. For selected recent papers on the synthesis of trans-azetidinones, see: (a) Wu, G.; Wong, Y.; Ding, Z. J. Org. Chem. 1999, 64, 3714. (b) Panunzio, M.; Bacchi, S.; Campana, E.; Fiume, L.; Vicennati, P. Tetrahedron Lett. 1999, 40, 8495. (c) Podlech, J.; Linder, M. R. J. Org. Chem. 1997, 62, 5873. (d) Podlech, J. Synlett. 1996, 582. (d) Browne, M.; Burnett, D. A.; Caplen, M. A.; Chen, L.-Y.; Clader, J. W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Viziano, M.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555.
49. For selected recent papers on the synthesis of trans-azetidinones, see: (a) Wu, G.; Wong, Y.; Ding, Z. J. Org. Chem. 1999, 64, 3714. (b) Panunzio, M.; Bacchi, S.; Campana, E.; Fiume, L.; Vicennati, P. Tetrahedron Lett. 1999, 40, 8495. (c) Podlech, J.; Linder, M. R. J. Org. Chem. 1997, 62, 5873. (d) Podlech, J. Synlett. 1996, 582. (d) Browne, M.; Burnett, D. A.; Caplen, M. A.; Chen, L.-Y.; Clader, J. W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Viziano, M.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555.
50. For selected recent papers on the synthesis of trans-azetidinones, see: (a) Wu, G.; Wong, Y.; Ding, Z. J. Org. Chem. 1999, 64, 3714. (b) Panunzio, M.; Bacchi, S.; Campana, E.; Fiume, L.; Vicennati, P. Tetrahedron Lett. 1999, 40, 8495. (c) Podlech, J.; Linder, M. R. J. Org. Chem. 1997, 62, 5873. (d) Podlech, J. Synlett. 1996, 582. (d) Browne, M.; Burnett, D. A.; Caplen, M. A.; Chen, L.-Y.; Clader, J. W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Viziano, M.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555.
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53. When the experiments were performed at lower temperature unreactive cis-2-azetidinones were observed. Complex reaction mixtures were detected when the reactions were carried out at higher temperatures.
54. The moderate yields obtained in some cases result from incomplete conversion of the starting material together with unidentified side reaction products.
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56. The assignment of relative stereochemistry based on the observed coupling constant for methine protons H3 and H4 is a very well stablished criterium in β-lactam chemistry. See, for example: (a) Ren, X. F.; Turos, E.; Lake, C. H.; Churchill, M. R. J. Org. Chem. 1995, 60, 6468. (b) Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (c) Zamboni, R.; Just, G. Can. J. Chem. 1979, 57, 1945.
57. The assignment of relative stereochemistry based on the observed coupling constant for methine protons H3 and H4 is a very well stablished criterium in β-lactam chemistry. See, for example: (a) Ren, X. F.; Turos, E.; Lake, C. H.; Churchill, M. R. J. Org. Chem. 1995, 60, 6468. (b) Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (c) Zamboni, R.; Just, G. Can. J. Chem. 1979, 57, 1945.
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64. Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.