10419-35-9Relevant articles and documents
Hydroxy-1-aminoindans and derivatives: Preparation, stability, and reactivity
Herzig, Yaacov,Lerman, Lena,Goldenberg, Willy,Lerner, David,Gottlieb, Hugo E.,Nudelman, Abraham
, p. 4130 - 4140 (2007/10/03)
The chemical stability and reactivity of hydroxy-1-aminoindans and their N-propargyl derivatives are strongly affected by the position of the OH group and its orientation relative to that of the amino moiety. Thus, the 4- and 6-OH regioisomers were found to be stable, while the 5-OH analogues were found to be inherently unstable as the free bases. The latter, having a para orientation between the OH and the amino moieties, could be isolated only as their hydrochloride salts. 7-Hydroxy-1-aminoindans and 7-hydroxy-1- propargylaminoindans represent an intermediate case; while sufficiently stable even as free bases, they exhibit, under certain experimental conditions, unexpected reactivity. The instability of the 5- and 7-hydroxy-aminoindans is attributed to their facile conversion to the corresponding, reactive quinone methide (QM) intermediates. The o-QM obtained from 7-hydroxy-aminoindans was successfully trapped with ethyl vinyl ether via a Diels-Alder reaction to give tricyclic acetals 32a,b.
A New Generation of o-Quinone Methides from o-(1-(Alkylthio)alkyl)phenols under Mild Conditions
Inoue, Tsutomu,Inoue, Seiichi,Sato, Kikumasa
, p. 653 - 656 (2007/10/02)
o-(1-(Alkylthio)alkyl)phenols are converted into o-quinone methides in good yield by treatment with silver oxide under mild conditions.Since the methides tend to prefer (E) configuration, cis-4-alkyl-2-alkoxychromans are exclusively obtained as a result o
