27410-89-5Relevant academic research and scientific papers
An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature
Deligeorgiev, Todor,Kaloyanova, Stefka,Lesev, Nedyalko,Vaquero, Juan J.
experimental part, p. 783 - 788 (2011/10/09)
A series of 2-alkylthio derivatives of hetaryl thiols were synthesized by selective S-alkylation with alkyl halides (bromides and iodides) with ultrasonic irradiation at room temperature. The reaction was found to be generally applicable to hetaryl thiol derivatives with different substituents in the aromatic nucleus and various alkyl halides. The reaction gives high to excellent yields of products with high purity.
Synthesis of 3-(2-Benzothiazolylthio)propanenitrile and Related Products
D'Amico, John J.,Suba, Lydia,Ruminski, Peter G.
, p. 1629 - 1635 (2007/10/02)
The reaction of 2-mercaptobenzothiazole, 2-mercaptobenzoxazole or 5-chloro-2-mercaptobenzothiazole with either acrylonitrile or acrylamide under basic conditions afforded the N-cyanoethylated products 1, 2 and 3 or the N-amidoethylated products 4, 5 and 6, respectively.The reaction of the sodium salts of the same thiazolethiols with 3-chloropropionitrile furnished a mixture containing the N-cyanoethylated products 1, 2 and 3 and the unknown S-cyanoethylated products 7, 8 and 9, respectively.Whereas, substituting 3-chloropropionamide for 3-chloropropionitrile in the same reaction gave only the S-substituted products 10, 11, and 12, respectively.The treatment of 10, 11 or 12 with phosphorus oxychloride or thionyl chloride in DMF afforded 7, 8 and 9 in excellent yields.Possible mechanisms and supporting nmr data are discussed.
BENZAZOLIN-2-THIONES IN THE MICHAEL REACTION. 2. REACTION OF BENZOTHIAZOLIN- AND BENZOXAZOLIN-2-THIONES WITH ACRYLONITRILE, ACRYLAMIDE, AND METHYL ACRYLATE IN THE PRESENCE OF BASIC CATALYSTS
Anan'eva, K. V.,Rozhkova, N. K.
, p. 564 - 567 (2007/10/02)
Depending on the structure of the reagents and the kind of basic catalyst, the addition of benzazolin-2-thiones to an activated double bond takes place at either nitrogen or sulfur.Acrylonitrile, regardless of the catalyst, reacts at the nitrogen atom.In the presence of sodium methylate, addition to acrylamide takes place only, and to methyl acrylate predominantly at nitrogen.In the presence of triethylamine, a mixture of compounds with a high content of S-derivatives forms.
BENZAZOLIN-2-THIONES IN THE MICHAEL REACTION. 1. REACTION OF BENZOTHIAZOLIN- AND BENZOXAZOLIN-2-THIONES WITH ACRYLONITRILE, ACRYLAMIDE, AND METHACRYLATE IN THE PRESENCE OF ACID CATALYST
Anan'eva, K.V.,Rozhkov, N.K.
, p. 456 - 459 (2007/10/02)
The reaction of benzothiazolin- and benzoxazolin-2-thiones with acrylonitrile, acrylamide, and methylacrylate under conditions of acid catalysis takes place at the sulfur atom.The formation of minor amounts of N-derivatives is attributed to izomerization of the principal reaction products.
