Synthesis of fragrant heterocyclic thioketo analogues of jasmone under microwave conditions

Abstract

Rapid, solvent-free and cleaner conversions of fragrant heteroketones, heterocyclic analogues of natural jasmone, to the corresponding thioanalogues were described. Obtained structures of thioketohetero derivatives are based on pyrrolidinone, oxazolidinone and thiazolidinone systems with saturated and 2-double or 2-triple unsaturated five-carbon side chain. Thionations were performed by the use of Lawesson's reagent without any solvent or solid support under microwave conditions with good yield. Odour evaluation and relationships between their chemical structure and osmic properties for all synthesized fragrant compounds have been studied. It has been shown that the majority of them have exhibited interesting, very intensive, durable and fixative fragrant properties.

Essential oil of Plectranthus tenuicaulis for flavour and fragrance: Synthesis of derivatives from natural and synthetic 6,7‐epoxyocimenes

“…The two subsequent chemical transformations concern the synthesis of S‐containing compounds which are usually known for their very high odour intensity . The first one describes the preparation of thiirane derivatives using potassium thiocyanate dissolved in polyethylene glycol 400 .…”

“…[28] The first one describes the preparation of thiirane derivatives using potassium thiocyanate dissolved in polyethylene glycol 400. [12] A nucleophilic addition of SCN -at the opposite side of the oxirane bridge led to (3S)-(5E)-2,6-dimethyl-2,3-epithioocta-5,7-diene 14 when applied to natural (R)-(E)-ocimene epoxide.…”

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

“…The significance of fragranced jasmone prompted Pawelczyk et al [22] to synthesize thio analogs of jasmones under solvent-free conditions. Consequently, it has also been found that replacing conventional methods with microwave solvent-free methods for the thionation of jasmone heterocyclic analogs to thio analogs have been observed in quite a bit of research literature due to its high-yielding, environmentally friendly, and economical procedures [21,23,24].…”

“…Their odors are unpleasant and spicy notes at first, which become better over time. These new synthetic odor notes have found a place in perfumery, flavor, and fragrance industries [24]. Further research in this field is imperative to make the perfume industry flourish.…”