Hydroxy-1-aminoindans and derivatives: Preparation, stability, and reactivity

Yaacov Herzig, Lena Lerman, Willy Goldenberg, David Lerner, Hugo E. Gottlieb, Abraham Nudelman

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)4130-4140
Number of pages11
JournalJournal of Organic Chemistry
Volume71
Issue number11
DOIs
StatePublished - 26 May 2006

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