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2011

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cc-by (c) Mesquida Estévez, Ma. Neus et al., 2011
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/120566

Synthetic approaches to multifunctional indenes

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https://doi.org/10.3762/bjoc.7.204

Abstract

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.

Subject

Síntesi orgànica, Compostos organometàl·lics, Compostos policíclics, Amides

Subject (English)

Organic synthesis, Organometallic compounds, Polycyclic compounds, Amides

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

Citation

MESQUIDA ESTÉVEZ, Ma. Neus, et al. Synthetic approaches to multifunctional indenes. Beilstein Journal of Organic Chemistry. 2011. Vol. 7, num. 1739-1744. ISSN 1860-5397. [consulted: 8 of August of 2026]. Available at: https://hdl.handle.net/2445/120566

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