Eucalyptol: a new solvent for the synthesis of heterocycles containing oxygen, sulfur and nitrogen

Abstract

We report here the first investigation of the use of eucalyptol as a new solvent for organic transformations.

Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles

“…As reusability of the solvent is essential from an economic and environmental perspective, we have shown its feasibility throughout the present study. This is in line with results from our previous work [2], wherein an average 70% solvent recovery (from using rotary evaporator system) was observed for each reaction series without noticeable loss of properties.…”

“…As per the reaction temperature level, we observed in collection of published results that the reported ranges of temperature were between 70-115°C. Nevertheless, our previous work showed that a reaction temperature from 100 °C was required to reach a total dissolution and consequently, a good reaction progress [2]. In this work, we established that the best temperature was 110 °C.…”

“…For the last few years, our team has been dedicated to and focused on the discovery of new solvents, as well as on the development of new methodologies and approaches for the synthesis of heterocycles using greener solvents. As demonstrated in our latest reported work, [2] eucalyptol can be an interesting, viable and sustainable alternative to common solvents. It is the main constituent of the essential oil of eucalyptus; a fast-growing tree that is experiencing a recrudescence at the plantation level due to its use in the paper industry.…”

Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents

“…They have shown that it could be an interesting alternative to conventional solvents for the one-pot synthesis of 2,3-diarylimidazol[1,2-a]pyridines involving a condensation between 2-aminopyridine and bromoacetophenones, followed by a C-H activation at C-3. This solvent, derived from biomass and recyclable, was also effective for various transformations of heteroatom-containing heterocycles such as oxygen, sulfur, or nitrogen (Scheme 54) [44].…”

Taming the Reactivity of Monoterpene Synthases To Guide Regioselective Product Hydroxylation

“…[1] Cineole (1,8-cineole; eucalyptol) is used in the flavour, fragrance, and cosmetics industries due to its pleasant minty aroma and cooling spicy taste, as well as jet-fuel precursor [2] and sustainable solvent for organic transformations. [3] Most known monoterpenoids, including cineole, are commonly produced by plants, where they play diverse roles in signalling and communication as well as defence against predatory species. [4] As a result, most known monoterpene cyclases/synthases (mTC/Ss) are of plant origin.…”