论文信息 - Amidrazones. Part 9. Convenient Synthesis 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.

Amidrazones. Part 9. Convenient Synthesis 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.

Abstract A simple, efficient procedure for the conversion of phenylhydrazine to 1-alkyl-1-phenylhydrazines via base-promoted hydrolysis of 1-alkyl-3-amino-4,5-dihydro-1-phenyl-1H-pyrazolium iodides (2) is described. N1, N1-disubstituted hydrazones of trans-cinnamamide and acrylamide are obtained by Hofmann-type ring openings of 1,1 -disubstituted-3-amino-4,5-dihydro-5-phenyl (or 5-unsubstituted) -1H-pyrazolium halides (5, 7).

[1] P. Smith. Derivatives of hydrazine and other hydronitrogens having N-N bonds , 1983 .

[2] A. J. Bellamy,et al. Synthesis and oxidation of some 1-alkenyl-1-phenylhydrazines and their 1,2-isomers , 1979 .

[3] W. Simons. The Sadtler handbook of proton NMR spectra , 1978 .

[4] M. Mąkosza,et al. Reactions of Organic Anions. LXX. Catalytic N-Alkylation of Phenylhydrazones in Aqueous Medium , 2002 .

[5] H. Dorn,et al. Über die Cyanäthylierung N‐monosubstituierter Hydrazine , 1965 .

[6] D. C. Iffland,et al. Oxidation of N,N-Disubstituted Ketohydrazones by Lead Tetraacetate. Carbon—Nitrogen Bond Cleavage1 , 1963 .

[7] L. Blangey,et al. 222. Über die Kondensation von asymmetrischen Alkyl- und Aryl-phenylhydrazinen mit 1,2-Naphthochinon) , 1946 .

[8] A. F. Crowther,et al. 21. The mechanism of indole formation from phenacylarylamines. Part I , 1943 .

[9] Herbert E. Carter,et al. ALKYLATION OF PHENYLHYDRAZINE IN LIQUID AMMONIA , 1941, The Journal of Organic Chemistry.

[10] C. Lenoir,et al. Bull. Soc. Chim. France , 1915 .