107798-95-8Relevant academic research and scientific papers
Nucleophilic Additions to Triazolinedione Ylides, Extremely Reactive Carbonyl Equivalents: A New Class of Condensation Reactions
Wilson, R. Marchall,Hengge, Alvan
, p. 2699 - 2707 (2007/10/02)
The ylides of N-phenyltriazolinedione (10 and 13) are readily prepared when the ylide carbon atom is substituted by phenyl or 3-methylindol-2-yl groups.In fact the indole-substituted ylide 10 is sufficiently stabile to be isolated in good yield when it is formed by the oxidation of the corresponding urazole 9 with tert-butyl hypochlorite followed by dehydrohalogenation with triethylamine.These triazolinedione ylides both undergo facile addition of nucleophiles at the ylide carbon atoms.In the case of nucleophilic addition by enolate species, the initial adducts undergo subsequent elimination of N-phenylurazole to form olefinic condensation products, while nucleophilic addition of pyrrole or n-butanethiol results in bis adducts in which two molecules of the nucleophile become attached to what had been the ylide carbon atom.The in situ generation of these triazolinedione ylides and subsequent transformations are operationally extremely simple procedures that frequently afford high product yields and as such would seen to offer considerable promise as synthetic methods.
THE CHEMISTRY OF AN AZOMETHINE IMINE DERIVED FROM 2,3-DIMETHYLINDOLE AND N-PHENYL TRIAZOLINEDIONE: A NEW AND FACILE CONDENSATION METHOD
Wilson, R. Marshall,Hengge, Alvan
, p. 3673 - 3676 (2007/10/02)
The urazole 3 derived from 2,3-dimethylindole and PTAD has been found to be converted readily to the unusually stable azomethine imine 5 with t-butylhypochlorite followed by elimination of HCl.This azomethine imine has been shown to serve as a carbonyl-equivalent in a number of aldol-type condensations under mild conditions.
