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Title: | One-pot organocatalyzed synthesis of tricyclic indolizines |
Author: | Zeoly, Lucas A. Acconcia, Lais V. Rodrigues, Jr., Manoel T. Santos, Hugo Cormanich, Rodrigo A. Paniagua, Juan Carlos Moyano i Baldoire, Albert Coelho, Fernando |
Keywords: | Catàlisi Química de l'aigua Isomerització Catalysis Water chemistry Isomerization |
Issue Date: | 14-Apr-2023 |
Publisher: | Royal Society of Chemistry |
Abstract: | Indolizines and their saturated derivatives are important structural motifs present in several biologically active compounds of both natural and synthetic origin. We describe herein a one-pot approach for the synthesis of tricyclic indolizines catalyzed by a bicyclic imidazole-alcohol. The protocol is based on an aqueous Morita-Baylis-Hillman reaction between pyridine-2-carboxaldehydes and six- or seven-membered cyclic enones, followed by sequential intramolecular cyclization and dehydration. So, in a single operational step two new bonds (C-C and C-N) are formed in an organocatalyzed process that takes place in simple conditions (stirring in water at 60 °C for 12 h) and with great atom economy (water as the sole byproduct), affording the purified compounds in yields ranging from 19 to 70%. The facility of the cyclization strongly depends on the size of the cycloalkenone ring: while MBH adducts derived from six-, seven- or eight-membered cycloenones are readily transformed into the corresponding indolizines, cyclopentenone-derived MBH adducts do not cyclize. A competition experiment revealed that cycloheptenone- derived MBH adducts cyclize faster than cyclohexenone-derived adducts. Model DFT calculations have been performed to rationalize these reactivity trends. |
Note: | Reproducció del document publicat a: https://doi.org/10.1039/d3ob00346a |
It is part of: | Organic & Biomolecular Chemistry, 2023, vol. 17, p. 1-15 |
URI: | http://hdl.handle.net/2445/200659 |
Related resource: | https://doi.org/10.1039/d3ob00346a |
ISSN: | 1477-0520 |
Appears in Collections: | Articles publicats en revistes (Ciència dels Materials i Química Física) Articles publicats en revistes (Institut de Química Teòrica i Computacional (IQTCUB)) |
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