38604-67-0

Upstream product

• 618-40-6 1-Methyl-1-phenylhydrazine 
• 109-94-4 formic acid ethyl ester 
• 100-61-8 N-methylaniline 
• 614-00-6 N-methyl-N-nitrosoaniline 

Downstream Products

• 350798-25-3 formic acid-(N,N'-dimethyl-N'-phenyl-hydrazide) 
• 29195-01-5 N'-methyl-N-methyl-N-phenylhydrazine 
• 61700-67-2 C₈H₈N₂ 
• 76579-56-1 N,N,N'-trimethyl-N'-phenylhydrazine 
• 1170697-26-3 benzoic acid N,N'-dimethyl-N'-phenylhydrazide 

Relevant academic research and scientific papers

Anionic [3,3], [2,3] and [1,2] rearrangements of aliphatic and aromatic acyl hydrazines with N-N bond cleavage

N-Acyl-N'-phenylhydrazines rearrange under basic conditions to afford α-aminophenylacetamides. This reaction can be rationalized in terms of [3,3] sigmatropic shifts of enolized intermediates. The Sommelet-Hauser-type and Stevens-type rearrangements of both aromatic and aliphatic acylhydrazines compete with the [3,3] rearrangement.

N-Isocyanodialkylamines generated in situ for the Joullié–Ugi reaction with indolenines

N-Isocyanodialkylamines are rare isocyanide surrogates for the Ugi-type reactions. To avoid problems with instability and the obnoxious smell of these reagents, we optimized and employed a convenient protocol for in situ dehydration of N,N-dialkyl-N′-formyl hydrazines to give the respective N-isocyanodialkylamines which were utilized in the reaction with indolenines and acetic acid. The reaction was demonstrated to give modest to excellent yields of products incorporating the N-isocyanodialkylamine but not the carboxylic acid component.