Functionalised Pyrazoles through a Facile One-Pot Procedure from N-Tosyl-N-propargylhydrazine and Aryl Iodides or Vinyl Triflates

Synlett

Volumn 1997, Issue 8, 1997, Pages 959-961

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Carangio, Antonella ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542782422     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-936     Document Type: Article

References (21)

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2. The Merck Index, Windholz, M., Ed.; Merck & Co.; 9th Edn. 1976.
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5. Berger, J.C., Iorio, L.C. Annu. Rep. Med. Chem. 1979, 14, 21; ibid. 1980, 15, 26.
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8. Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289; Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron 1993, 49, 4955; Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1993, 65; Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581.
9. Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289; Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron 1993, 49, 4955; Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1993, 65; Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581.
10. Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289; Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron 1993, 49, 4955; Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1993, 65; Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581.
11. +, 1), 91 (100).
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15. +, 37), 234 (100).
16. 4-5 (2.5 Hz) only for the proton at C-4. Replacement of hydrogen with methyl at the nitrogen atom of 4d (methylation of 4b affords the corresponding 1-N-methyl derivative in 64% yield) leads to a fixed structure whose protons at C-4 and C-5 appear as doublets (J = 2.2 Hz) at δ 6.15 and 7.41.
17. Chenon, M.T.; Coupry, C.; Grant, D.M.; Pugmire, R.J. J. Org. Chem. 1977, 42, 659; Nesmeyanov, A.N.; Zavelovich, E.B.; Babin, V.N.; Kochetkova, N.S.; Fedin, E.I. Tetrahedron 1975, 31, 1461.
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19. +, 8), 145 (92), 115 (100).
20. Even under these conditions some irreproducibility was observed when the isolation of the coupling derivative was attempted. An apparently identical preparation gave 3a in 30% yield.
21. +, 40), 159 (100).