Richard F. Smith

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

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).

AMIDRAZONES. 8. SYNTHESIS OF 1,2,4-OXADIAZOLES BY THERMOLYSIS OF N3-ACYLAMIDRAZONE YLIDES

N3-Acylamidrazone ylides 3 were synthesized by the reaction of 2-(iminophenylmethyl)-1,1,1-trimethylhydrazinium hydroxide, inner salt (2a) or 2-(1-iminoethyl)-1,1,1-trimethylhydrazinium hydroxide, inner salt (2b) with acyl chlorides or acetic anhydride. Thermolysis of 3 gave 3,5-disubstituted oxadiazoles 4 and trimethylamine.

Amidrazones 10. Stevens rearrangement of 1-benzyl and 1-allyl-substituted-3-amino-4,5-dihydro-1-phenyl-1H-pyrazolium bromides

Abstract 2-Benzyl-3-imino-1-phenylpyrazolidine (5a) and 2-allyl-3-imino-1-phenylpyrazolidine (5b) are obtained by the base-promoted rearrangement of the title compounds (4a and 4b).

Base-Promoted Elimination Reactions of Acetaldehyde N-Alkyl-N,N-Dimethylhydrazonium Salts. A Convenient Synthesis of N,N-Dimethylalkylamines

Abstract The title reaction was utilized for efficient conversion of SN2-reactive alkyl halides to the corresponding N,N-dimethylaIkylamines.

Amidrazones V. thermolysis of N1-benzyl-substituted amidrazone ylides

Abstract Thermolysis of 1,1-dimethyl-1-benzyl-2-(iminophenylmethyl)hydrazinium hydroxide inner salt gave dimethylamine, 2,4,6-triphenyl-s-triazine and 2,4,6-triphenyl-1,2-dihydro-s-triazine.

Amidrazones 13. A Convenient Method for the Preparation of 1-Alkyl-1-methylhydrazines

Abstract An efficient one-pot procedure for the preparation of 1-alkyl-1-methylhydrazines from methylhydrazine via base-promoted hydrolysis of 1-alkyl-3-amino-4, 5-dihydro-1-methyl-1H-pyrazolium halides (3) is described.

An Efficient Microscale Procedure for the Preparation of 3,5-Dinitrobenzoates

A convenient microscale procedure for the preparation of 3,5-dinitrobenzoates, which utilizes 3,5-dinitrobenzoic acid and tosyl chloride in pyridine as an acylating medium, is described.