Reaction of 3-Methyl-2-cyclopenten-1-one N,N-Dimethylhydrazone with α,β-Unsaturated Carbonyl Compounds. A Novel Synthesis of Bicyclic Compounds

Abstract

3-Methyl-2-cyclopenten-1-one N,N-dimethylhydrazone reacted with methyl vinyl ketone or acrylic acid derivatives to give a new bicyclic bifunctional compound in good yield in a polar aprotic solvent such as dimethylformamide.

ChemInform Abstract: Synthesis of Bicyclic N‐Methylpyrazoline and Pyrazole Derivatives from α,β‐Unsaturated Ketones and N,N‐Dimethylhydrazine: An Illustration of Reductive Cyclization.

“…A thorough literature survey reveals that there are only a few reports of the reaction of dimethylhydrazine with a,b-unsaturated ketones, which led to the corresponding hydrazone derivatives. Matsumiya et al prepared a dimethylhydrazone derivative of 3-methyl-2-cyclopenten-1-one [14]. A number of acyclic dimethylhydrazone derivatives of 4-phenyl-3buten-2-ones were obtained as a mixture of E and Z isomers [15,16], and efforts were made to separate the geometrical isomers [16].…”

Synthesis of Bicyclic N‐Methylpyrazoline and Pyrazole Derivatives from α,β‐Unsaturated Ketones and N,N‐Dimethylhydrazine: An Illustration of Reductive Cyclization

“…Matsumiya et al . prepared a dimethylhydrazone derivative of 3‐methyl‐2‐cyclopenten‐1‐one . A number of acyclic dimethylhydrazone derivatives of 4‐phenyl‐3‐buten‐2‐ones were obtained as a mixture of E and Z isomers , and efforts were made to separate the geometrical isomers .…”