3161-47-5Relevant academic research and scientific papers
2-Phenyl-4-bis(methylthio)methyleneoxazol-5-one: Versatile template for diversity oriented synthesis of heterocycles
Amareshwar, Vijayalaxmi,Mishra, Nimesh C.,Ila, Hiriyakkanavar
experimental part, p. 5793 - 5801 (2011/10/01)
4-Bis(methylthio)methylene-2-phenyloxazol-5-one (1) has been shown to be a versatile template for the synthesis of novel heterocyclic scaffolds. The key protocol involves nucleophilic ring opening of 1 with various primary aliphatic, aromatic amines and diamines to give open-chain amide adducts which are transformed into 4-bis(methylthio)methylene-2-phenyl-1-alkyl/arylimidazol-5-(4H) -ones (5) in good yields in the presence of anhydrous NaOAc/AcOH. Similarly, the amide adducts 4h-i from 3,4-dimethoxyphenylethylamine and tryptamine undergo interesting rearrangement in the presence of POCl3 to furnish 1-(2-phenyl-5-methylthio-4-thiazolyl)dihydroisoquinoline and β-carboline derivatives 8-9 in good yields. The amide adduct 14 from o-phenylenediamine on exposure to refluxing acetic acid or in the presence of Ag2CO 3 affords substituted 3H-1,5-benzodiazepinone, 2-(5-methylthio-2- phenyl-4-oxazolyl)-1H-benzimidazole and trisubstituted oxazole (15-17), whereas the bis-adduct from ethylenediamine yields ethylene bridge tethered bis-imidazole 23 and bis-oxazole 24 under similar reaction conditions. Probable mechanisms for the formation of various products have been suggested.
4-Bis(methylthio)methylene-2-phenyloxazol-5-one: Versatile template for synthesis of 2-phenyl-4,5-functionalized oxazoles
Misra, Nimesh C.,Ila
supporting information; experimental part, p. 5195 - 5202 (2010/10/21)
(Figure presented) 4-Bis(methylthio)methylene-2-phenyloxazol-5-one has been shown to be a versatile template for the synthesis of various 2-phenyl-3,4-substituted oxazoles via nucleophilic ring-opening of oxazolone with various oxygen, nitrogen, and carbo
A Facile Synthesis and Solvolysis of 4-methylene-2-phenyl-2-oxazolin-5-one
Tripathy, Pradeep K.,Roy, Jalpana,Mukerjee, Arya K.
, p. 1275 - 1276 (2007/10/02)
2-Phenyl-2-oxazolin-5-one, generated in benzene by cyclising hippuric acid (1) with ethyl chloroformate in the presence of triethylamine, affords 4-bis(methylthio)methylene-2-phenyl-2-oxazolin-5-one (2), on reaction with carbon disulphide and subsequent methylation with methyl iodide in the presence of triethylamine.All these reactions occur in one-pot.Hydrolysis and alcoholysis of 2 give the acid (3a) and the esters (3b,c), respectively.
ONE-FLASK SYNTHESIS OF 4-(BIS(METHYLTHIO))METHYLENE-2-PHENYL-5-OXO-4,5-DIHYDRO-1,3-OXAZOLE AND ITS AMINOLYSES
Ashare, Ram,Roy, Jalpana,Mukerjee, Arya K.
, p. 1325 - 1329 (2007/10/02)
Cyclization of hippuric acid with ethyl chloroformate and triethylamine in benzene and subsequent triethylamine-mediated condensation with carbon disulphide and S-methylation afford the title compound which undergoes 1,5-bond cleavage on heating with molar proportion of a primary amine in the presence of glacial acetic acid, the ketenethioacetal moiety remaining intact.On increasing the proportion of the amine and heating the mixture for a longer period, the corresponding N,N'-disubstituted benzoylaminomalondiamides are obtained.
