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Synthetic approaches to multifunctional indenes

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Alcalde Pais, Ma. Ermitas (María de las Ermitas)

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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.

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Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1739-1744

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cc-by (c) Mesquida Estévez, Ma. Neus et al., 2011

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

# metadata.dc.title[].value
Synthetic approaches to multifunctional indenes