94287-38-4Relevant academic research and scientific papers
X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 13 PROTOTROPIC GENERATION OF AZOMETHINE IMINES FROM HYDRAZONES
Grigg, Ronald,Dowling, Marie,Jordan, Maurice W.,Sridharan, Visuvanathar,Thianpatanagul, Sunit
, p. 5873 - 5886 (2007/10/02)
Hydrazones of aldehydes and ketones undergo to intermolecular cycloaddition to electronnegative olefins via azomethine imines, formed by a formal 1,2-prototropic shift, in low to moderate yield on heating in xylene or ethanol.In some instances the reaction is diverted to give products derived (at least formally) from an ene reaction.Similar intramolecular cycloadditions occur with unactivated terminal alkenes and alkynes.
APPLICATIONS OF THE THERMAL ENE REACTION OF ALDEHYDE t-BUTYL- AND PHENYL- HYDRAZONES
Baldwin, Jack E.,Adlington, Robert M.,Jain, Ashok U.,Kolhe, Jayant N.,Perry, Matthew W. D.
, p. 4247 - 4252 (2007/10/02)
The Thermal Ene reaction of aldehyde t-butyl- and phenyl- hydrazones with enophiles gave C-trapped azo-adducts which can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, γ-alkyl-2-pyrrolidones, and γ-amino-esters.
Michael Additions of Hydrazones for Carbon-Carbon Bond Formation
Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Jain, Ashok U.,Kolhe, Jayant N.,et al.
, p. 1095 - 1096 (2007/10/02)
The lithium salts of t-butyl- and trityl-hydrazones react with methyl crotonate to form C-trapped azo-esters and similar products were observed from a thermal ene-reaction of aldehyde t-butylhydrazones with methyl acrylate or acrylonitrile, and aldehyde phenylhydrazones with methyl acrylate; these products can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, saturated esters, γ-alkyl-2-pyrrrolidones, and γ-amino-esters.
