Synthetic approaches to multifunctional indenes

The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2011-12, Vol.7 (1), p.1739-1744
Main Authors: Mesquida, Neus, López-Pérez, Sara, Dinarès, Immaculada, Alcalde, Ermitas
Format: Article
Language:English
Subjects:
aldol reaction
Amides
Chemistry
Compostos organometàl·lics
Compostos policíclics
Full Research Paper
indanones
indenes
Organic synthesis
Organometallic compounds
organometallic reagents
Polycyclic compounds
Síntesi orgànica
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Summary:The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3-indenyl)acetamides as key intermediates. Although several multistep synthetic approaches can be applied to obtain these advanced intermediates, we describe herein their preparation by an aldol-type reaction between 5-nitroindan-1-ones and the lithium salt of N,N-disubstituted acetamides, followed immediately by dehydration with acid. This classical condensation process, which is neither simple nor trivial despite its apparent directness, permits an efficient entry to a variety of indene-based molecular modules, which could be adapted to a range of functionalized indanones.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.204