Catalytic condensation of 3-carene with formaldehyde

Sidorenko, A.Yu.; Kurban, Yu.M.; Khalimonyuk, T.V.; Il'ina, I.V.; Li-Zhulanov, N.S.; Patrusheva, O.S.; Goltsova, V.V.; Bei, M.P.; Ihnatovich, Zh.V.; Wärnå, J.; Volcho, K.P.; Salakhutdinov, N.F.; Murzin, D.Yu.; Agabekov, V.E.

doi:10.1016/j.mcat.2023.113627

Cited by 3 publications

(2 citation statements)

References 44 publications

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“…By opening synthetic access to compound 17 , we made it possible, for the first time, to study its reaction with salicylic aldehyde 10a . Here we used commercially available aluminosilicate montmorillonite K10 as a catalyst, which was previously successfully employed for reaction of various monoterpenes and carbonyl compounds. ,− ,− The reaction was carried out in one preparative step without solvent and at room temperature. Considering that α-terpineol and limonene 9 react similarly with aldehydes in the presence of acid catalysts,7 one would expect similar reactivity of compounds 12 and 17 .…”

Section: Resultsmentioning

confidence: 99%

“…In particular, trans -4-hydroxymethyl-2-carene 5 obtained via the reaction of 3-carene with formaldehyde , reacts with aldehydes in the presence of montmorillonite clays forming oxygen-containing heterocyclic compounds. The hydroxymethyl fragment is always involved in this transformation, and the product’s backbone significantly depends on the starting aldehyde’s structure.…”

Section: Introductionmentioning

confidence: 99%

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Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Ilyina,

Patrusheva,

Goltsova

et al. 2024

J. Org. Chem.

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Chiral oxygen-containing heterocyclic compounds are of great interest for the development of pharmaceuticals. Monoterpenes and their derivatives are naturally abundant precursors of novel synthetic chiral oxygencontaining heterocyclic compounds. In this study, acid catalyzed reactions of salicylic aldehydes with (−)-8-acetoxy-6-hydroxymethyllimonene, readily accessible from α-pinene, leads to the formation of chiral polycyclic products of various structural types. Three of the six isolated chiral heterocyclic products obtained from salicylic aldehyde contain previously unknown polycyclic ring types. Having carried out the reaction in the presence of Brønsted or Lewis acids (Amberlyst 15, trifluoromethanesulfonic acid, trifluoroacetic acid and boron trifluoride etherate) or aluminosilicates (montmorillonite K10, halloysite nanotubes), we found that the nature of products depends on the catalyst as well as the reaction conditions (reaction time, reactant ratio, presence or absence of solvent). Detailed mechanistic insight on the complex cascade reactions for product formation is provided with extensive experimental and quantum mechanical computational studies.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Ilyina,

Patrusheva,

Goltsova

et al. 2024

J. Org. Chem.

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Upgrading biomass to high-added value chemicals: synthesis of monoterpenes-based compounds using catalytic green chemical pathways

Sánchez-Velandia,

Gallego-Villada,

Mäki-Arvela

et al. 2024

Catalysis Reviews

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Novel Catalytic Systems for Condensation of Monoterpene Compounds with Aldehydes (A Review)

Sidorenko,

Agabekov

2024

Žurnal obŝej himii

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New catalysts for the Prins condensation of renewable monoterpene compounds with aldehydes were considered. Effective catalytic systems were functionalized zeolites, oxides, clays, halloysite and carbon nanotubes, organometallic structures and heteropolyacids, which make it possible to obtain target products with high selectivity. A number of compounds synthesized using such systems are used in perfumery, have high pharmaceutical potential and are platform molecules for further synthesis.

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Catalytic condensation of 3-carene with formaldehyde

Cited by 3 publications

References 44 publications

Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Upgrading biomass to high-added value chemicals: synthesis of monoterpenes-based compounds using catalytic green chemical pathways

Novel Catalytic Systems for Condensation of Monoterpene Compounds with Aldehydes (A Review)

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