A New Method for the Preparation of 4,5‐Substituted Δ⁴‐Oxazoline‐2‐Thiones

Abstract

SAMENVATTINGEen nieuwe methode voor de bereiding van 4,5-gesubstitueerde n4-oxazoline-2-thionen wordt beschreven. Uitgaande van benzolnen of acyloinen en thiocyaanzuur (of de zouten hiervan en een zuur) worden met goedeopbrengsten 4-oxazoline-2-thionen bekomen. In sommige gevallen vornien zich de isomere ~4-thiazolin-2-onen als nevenprodukten. Enkele gegevens over r. R. spectra en vormingsmechanisme worden eveneens vermeld.

N-Methylimidazole-Promoted Efficient Synthesis of Functionalized 1,3-Oxazoline-2-thiones under Solvent-Free Conditions

“…1,3-Oxazoline-2-thiones possess a simple heterocyclic frame which has been barely explored compared to its nonaromatic counterpart 1,3-oxazolidine-2-thione, with only relatively simple precursors related to a-hydroxyketones having been converted into 1,3-oxazoline-2-thiones. 1,2 Syntheses of 1,3-oxazoline-2-thiones have been reported using condensation of either thiocyanic acid [3][4][5][6] or isothiocyanates 7 with an a-hydroxycarbonyl substrate, or condensation of thiophosgene with an aminoketone. 8 The balance of reactivity of a-hydroxycarbonyl systems with thiocyanic acid toward the formation of either 1,3-oxazolidine-2-thione or 1,3-oxazoline-2-thione has been reported recently.…”

An updated review of fatty acid residue-tethered heterocyclic compounds: synthetic strategies and biological significance

“…The α-hydroxy ketone of oleic acid 77 was achieved in accordance with the method published by Brous and Lefort 38 via the oxidation of methyl cis -9,10-epoxyoctadecanoate 76 with dimethyl sulfoxide at 90–100 °C in the presence of boron trifluoride, which was cyclized to obtain the thioimidazoline derivative 78 through the method published by Vandenberghe and Willems procedure 39,40 (Scheme 15).…”

Nano ZnO Promoted Synthesis of 1,3-Oxazoline-2-Thione Derivatives

“…[4][5][6][7] A number of methods have been developed to synthesise 1,3-oxazolidine-2-thiones. [8][9][10][11][12][13][14][15][16][17][18] In this work, we combine 1-3 in the presence of N-methylimidazole and ZnO NPs to obtain the desired product 4 (Scheme 1).…”