tert-Butyl nitrite induced radical dimerization of primary thioamides and selenoamides at room temperature

• Published in: Tetrahedron letters Vol. 59; no. 3; pp. 272 - 276
• Main Authors: Chauhan, Swati, Chaudhary, Priyanka, Singh, Adesh Kumar, Verma, Pratibha, Srivastava, Vandana, Kandasamy, Jeyakumar
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.01.2018; Elsevier
• Subjects: ambient temperature; chemical structure; Chemistry; Chemistry, Organic; Dimerization; Green chemistry; nitrites; Physical Sciences; Science & Technology; tert-Butyl nitrite; Thiadiazoles; thioamides; Thiobenzamides; Thiadiazoles; tert-Butyl nitrite; Green chemistry; Thiobenzamides; Dimerization; OXIDATIVE DIMERIZATION; BOND-CLEAVAGE; ARYLBORONIC ACIDS; MEDICINAL CHEMISTRY; 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES; METAL; DERIVATIVES; N-NITROSAMINES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.12.033

[Display omitted] •Dimerization of thioamides and seleoamides was achieved with tert-butyl nitrite.•Reaction proceeds under catalyst and metal free conditions at room temperature.•Reaction proceeds through radical mechanism.•Easy operation, broad substrate scope and efficient conversion are the advantages. A simple and efficient method for the dimerization of primary thioamides into 1,2,4-thiadiazoles using tert-butyl nitrite is described. The optimized condition was also found to be suitable for the dimerization of benzoselenoamides into 1,2,4-selenadiazoles. All the reactions proceed smoothly at room temperature and gave the desired products in excellent yields in a short span of time.