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

Richard F. Smith Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

Laurie A. Olson Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

William J. Ryan Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

Karen J. Coffman Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

Julienne M. Galante Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

Timothy S. Wojdan Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

Patricia A. Mallardi Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

Thomas P. Eckert Department of Chemistry, State University College of Arts and Science Geneseo, New York, 14454

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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).

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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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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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