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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 5
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Original Articles

Amidrazones 9. Convenient Syntheses of 1-Alkyl-1-Phenylhydrazines and α,β-Unsaturated Amidrazones Via Base-Promoted Reactions of 1,1-Disubstituted-3-Amino-4,5-Dihydro-1H-Pyrazolium Salts

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Pages 585-596 | Published online: 19 Dec 2006

References

  • Smith , R. F. , Coffman , K. J. and Geer , S. M. 1983 . J. Heterocyclic Chem. , 20 : 69 Paper 8
  • Dorn , H. 1980 . Khim. Geteroskl Soedin , : 3 For a recent review see
  • Duffin , G. F. and Kendall , J. D. J. Chem. Soc. , 1954 408
  • Smith , P. A. S. 1983 . Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds , 28 – 32 . Benjamin/Cummings Publishing Company . For a review of 1,1-disubstituted hydrazine syntheses see Reading, Mass
  • Unpublished observations from our laboratories have established that 1-allyl- and 1-benzylphenylhydrazine cannot be prepared by this procedure. The salts (2, R = CH2CH=CH2 and CH2C6H5) undergo base-promoted Stevens rearrangements to give l-phenyl-2-(allyl or benzyl) -3-iminopyrazolidines.
  • Bellamy , A. J. and MacLean , L. 1979 . J.C.S., Perkin I , : 204
  • Bouchet , P. , Elguero , J. and Jacquier , R. 1966 . Jr., J. Org. Chem. , 31 : 1704 The related conversions of 1,1-disubstituted-3-oxo-pyrazolidinium salts and their conjugate bases (aminimides) to αa,β-unsaturated hydrazides have been reported
  • Barascut , J. L. , Elguero , J. and Jacquier , R. 1970 . Bull. Soc. Chim. France , : 1572 Obtained in 76% yield, mp 172–174°; C (from ethanol) by the reaction of methylhydrazine with cinnamonitrile using the procedure employed by The 1 H NMR spectral data obtained by us correlated with that reported by the French workers who reported mp 120–123° C for this compound
  • Gol'din , G. S. , Maksakova , M. V. and Kol'tsova . 1973 . Zh. Obschch. Khim. , 43 : 321
  • Le Berre , A. and Porte , C. 1976 . Bull. Soc. Chim. France , : 476 These workers prepared the chloride, iodide (no mp reported) and tosylate salts and reported these salts undergo complex decomposition in base
  • Linneman , A. 1877 . Ber. , 8 : 1095
  • Elguero , J. , Jacquier , R. and Mondon , S. 1970 . J. Chim. Soc. France , : 1576 For a detailed description of the 1H NMR spectra of 3-dimethylamino-substituted analogs see:
  • Dorn , H. , Zubek , A. and Hilgetag , G. 1965 . Chem. Ber. , 99 : 3377
  • Audrieth , L. F. , Weisiger , J. R. and Carter , H. E. 1941 . J. Org. Chem. , 6 : 417
  • Jonczyk , A. , Wlostowska , J. and Makosza , M. 1976 . Synthesis , : 795
  • Iffland , D. C. and Cerda , E. 1963 . J. Org. Chem. , 28 : 2769
  • Fierz-David , H. E. , Blangley , L. and Kaul , H. 1946 . Helv. Chim. Acta , 29 : 1765
  • Crowther , A. F. , Mann , F. G. and Purdie , D. 1943 . J. Chem. Soc. , : 58
  • 1978 . The Sadtler Handbook of Proton NMR Spectra , 229 Philadelphia : Sadtler Research Laboratories . Identical with the spectrum of sodium 3-hydroxypropanoate reproduced in

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