74553-37-0Relevant 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.
Intramolecular 1,3-Dipolar Cycloadditions and Intramolecular Ene Reactions of 2-(Alkenyloxy)benzaldehyde Arylhydrazones
Shimizu, Tomio,Hayashi, Yoshiyuki,Kitora, Yoshitaka,Teramura, Kazuhiro
, p. 2450 - 2455 (2007/10/02)
2-(3-Aryl-2-propenyloxy)benzaldehyde (or 1-naphthaldehyde) arylhydrazones undergo an intramolecular cycloaddition reaction via their 1,3-dipolar tautomers, azomethine imines, to the alkenyl group.Initial cycloadducts were converted to dehydrogenated compounds under the reaction conditions.On the other hand, introduction of cyano or ethoxycarbonyl groups instead of the aryl group into 3-position of the ortho propenyloxy group gave 3-cyanomethyl-4-chromanone arylhydrazones or the corresponding ethoxycarbonyl derivatives, respectively.The formation of these hydrazones was interpreted in terms of intramolecular ene reaction.The course of the reactions depends on the nature of the alkenyl substituents.
CYCLOADDITIONS INTRAMOLECULAIRES CATIONIQUE 3+ + 2 ET DIPOLAIRE-1,3 DE PHENYLHYDRAZONES.
Fouchet, B.,Joucla, M.,Hamelin, J.
, p. 1333 - 1336 (2007/10/02)
In acidic medium, alkenyl phenylhydrazones lead, probably via a 3+ + 2 cationic cycloaddition, to fused ring system, which are difficult to obtain as primary products of thermal 1,3 dipolar cycloaddition.
