One-step synthesis of oxazolidine-2-thiones in dimethyl sulphoxide

Abstract

The Knorr reaction when conducted in an aprotic polar solvent provides a new route to oxazolidine-2-thiones.REACTION of a-amino-alcohols with carbon disulphide in basic aqueous or alcoholic media is known1 to give either an oxazolidine-2-thione or a thiazolidine-2-thione depending on the structure of the amino-alcohol.2 The route taken by the reaction in aqueous KOH in refluxing CS, is constrained by the steric requirements of the carbon bearing the hydroxygroup. Thus primary alcohols react to give thiazolidine-2thiones, whereas amino-alcohols with a sterically hindered hydroxy-group give oxazolicline-2-thione.Anlino-alcohol R1 R2 R3 R4 M.p. Yield CH20H.CH2NH2

Primary Alkyl Amines as Latent Gelators and Their Organogel Adducts with Neutral Triatomic Molecules

“…Salts 2 − 5 were prepared as described in the Experimental Section and as outlined in Scheme . Reaction of primary amines with CO 2 and CS 2 leads to alkylammonium alkylcarbamates ( 2 ) 27-30 and alkylammonium alkyldithiocarbamates ( 5 ), respectively. Their spectroscopic properties are consistent with the assigned structures, and elemental analyses for 2c and 5c are as well.…”

Synthesis of Symmetrical N,N‘-Disubstituted Thioureas and Heterocyclic Thiones from Amines and CS2 over a ZnO/Al2O3 Composite as Heterogeneous and Reusable Catalyst

“…Thus, oxazolidine-2-thiones 7 and 8 , 1-mercaptobenzothiazole 9 , and imidazolidine-2-thione 10 were synthesized in high yield and in short reaction time, avoiding use of strong homogeneous acids and bases.…”

“…3,4-Dimethyloxazolidine-2-thione (8) : yield 1.21 g (92%), white solid; mp 121−2 °C (lit . mp 123 °C).…”

Effet d'engrenage. VIII. Extension à des dérivés fonctionnels de l'alanine

“…La reaction entre la cetone brom6e et le dithiocarbamate qui conduit au compose (A) puis la A,-thiazolinethione-2 (C), est un cas particulier de la reaction de Hantzsch (8,28).…”