106808-33-7Relevant academic research and scientific papers
Sels de N-alcoxypyridinium porteurs d'une fonction cetone dans leur chaine alcoxyle: Synthese et reactivite vis-a-vis d'amines secondaires
Sliwa, Henri,Randria-Raharimanana, Clarisse
, p. 1569 - 1574 (2007/10/02)
Reaction of α-bromoisobutyrophenone on pyridine 1-oxide and γ and β-picoline 1-oxide, in the presence of silver nitrate, leads to N-alkoxypyridinium and picolinium salts, bearing a keto group on their alkoxyl chain.On treatment with pyrrolidine, these salts are converted to 4-ω-pyrrolidinobutadienyl-3-isoxazolinols, substituted or not by a methyl group in their chain.The reaction proceeds according to the PARC-ANRO mechanism (Proton Abstraction, Ring Closure-Addition of a Nucleophile, Ring Opening), as demonstrated by isolation of the bicyclic isoxazolino pyridinium intermediates which result from the first phase of this process.In addition, steric hindrance towards ring opening caused by the methyl group in the adduct derived from β-picolin N-oxide, allow observation of a competiting novel mode of fragmentation alkoxylogous of Katritzky's mode A of decomposition of N-alkoxypyridinium salts.
EVIDENCE FOR A PARC-ANRO MECHANISM IN HETEROCYCLIC RING CONVERSION OF FUNCTIONALIZED N-ALKOXYPYRIDINIUM SALTS
Sliwa, Henri,Raharimanana, Clarisse
, p. 349 - 352 (2007/10/02)
Isolation of intermediate isoxazolopyridinium salts ascertains earlier mechanistic assumption in a heterocyclic ring conversion of potential value for a new approach to terpenoid synthesis.
