β-Tosylhydrazono phosphonates in organic synthesis. An unambiguous entry to polysubstituted pyrazoles

Synlett

Volumn , Issue 3, 1999, Pages 299-302

  Almirante, N ^a   Benicchio, A ^a   Cerri, A ^a   Fedrizzi, G ^a   Marazzi, G ^a   Santagostino, M ^a  

^a Prassis Sigma Tau Research Institute   (Italy)

Author keywords

Aldehyde; Pyrazole; , unsaturated tosylhydrazone; Tosylhydrazono phosphonate

Indexed keywords

ALDEHYDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; PHOSPHONIC ACID DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033020246     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2608     Document Type: Article

References (13)

1. Elguero J. Comprehensive Heterocyclic Chemistry Katritzky A. R., Rees C. W. Eds.; Pergamon Press: Oxford, 1984; Vol. 5, pp 167-303.
2. Beam C.F., Sandifer RM., Foote R.S., Hauser C.R. Synth. Comm. 1976, 6, 5-10 and references therein.
3. Almirante N., Cerri A., Fedrizzi G., Marazzi G. and M. Santagostino Tetrahedron Lett. 1998, 39, 3287.
4. Several distinct routes to β-keto phosphonates have been identified: Delamarche I. and Mosset P. J. Org. Chem. 1994, 59, 5453.
5. β-keto phosphonates precursors of β-tosylhydrazono phosphonates are commercially available (for 1a-c) or can be prepared according to published procedures: Aboujaoude E.E., Collignon N. and Savignac P. J. Organomet. Chem. 1984, 264, 9 (for 1f),
6. Clark R.D., Kozar L.G. and Heathcock C.H. Synthesis, 1975, 635 (for 1g),
7. Calogeropoulou T., Hammond G.B. and Wiemer D.F. J. Org. Chem. 1987, 52, 4185 (for 1h).
8. Arbuzov B.A. Pure Appl. Chem. 1964, 9, 307.
9. Hulme A.N., Howells G.E. and Walker R.H. Synlett 1998, 828 and references quoted.
10. Baker T.J. and Wiemer D.F. J. Org. Chem. 1998, 63, 2613 and references quoted.
11. Shapiro R.H., Heath M. J. Am. Chem. Soc. 1967, 89, 5734.
12. Only the (E)-isomer of β-monosubstituted α,β-unsaturated tosylhydrazones cyclize to pyrazole under the described conditions. See ref. 3.
13. For a review of the effects of structural changes in the phosphoryl and carbonyl components on the (E)/(Z) ratio see Organic Reactions Vol. 25 Wadsworth W.S. pp 81-85.