ChemInform Abstract: Aryl(1‐benzoylamino‐2,2‐dichlorovinyl)sulfones.

Abstract

The title compounds (III) have been prepared for the first time.

Reaction of 1-tosyl-2,2-dichloroenamines with the Lawesson’s reagent

“…To a solution of 0.0035 mol of compound Ia [1] in 50 ml of dioxane was added 0.0035 mol of Lawesson's reagent. The mixture was heated for 8 h at 100°C, the solvent was removed in a vacuum, to the residue was added 100 ml of saturated solution of sodium hydrogen carbonate, and the mixture was kept for 3 h at 20°C.…”

“…This fact was used for the synthesis of a number of the previously unknown bifunctionally substituted 4,5-thiazoles.Previously we studied the reaction of the enamides of type I with the highly basic amines [1] and sodium hydrosulfide [2], which leads to the derivatives of 5-amino-5-mercaptooxazole, the agonists of 5-NT6 receptors [3].In this work we for the first time studied the interaction of the enamides I with the Lawesson's reagent leading to the 2-R-4-tosyl-5-chloro-1,3-thiazole derivatives III. The chlorine atom in compounds III shows significant lability towards the action of the highly basic amines, sodium phenolate, and thiophenoxides, undoubtedly due to the influence of electronacceptor groups in the vicinal position to the halogen atom.…”

“…Previously we studied the reaction of the enamides of type I with the highly basic amines [1] and sodium hydrosulfide [2], which leads to the derivatives of 5-amino-5-mercaptooxazole, the agonists of 5-NT6 receptors [3].…”

N-methyl-D-glucamine-derived 4-substituted 1,3-oxazoles

“…Later the reaction was used for the preparation of 5-amino-1,3-oxazoles containing ester [18], phosphonyl [19], sulfonyl [20], and other group in the position 4. In [21] it was shown that dichloroacrylonitriles I also reacted with monoethanolamine and other amino alcohols to form the corresponding 1,3-oxazoles.…”

Derivatives of 5-(Dimethylamino)-4-tosyl-1,3-oxazole-2-carbaldehyde and Its Analogs

“…The first stage of this process is a particular case of fairly general cyclocondensations of enamides like Cl 2 C=C(Y)NHC(O)R with primary and secondary amines. The range of enamides suitable for preparing 5-amino-1,3-oxazole derivatives is very broad, since Y = C(O)OAlk, CN, P(O)(OAlk) 2 , P(O)Ar 2 , + PPh 3 Cl ! , SO 2 Alk, SO 2 Ar and other electronacceptor groups [7].…”