Study on the synthesis of thioamides from aldehyde N-tert-butylsulfinyl amide and sulfur in aqueous media
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https://doi.org/10.54939/1859-1043.j.mst.76.2021.54-60Keywords:
Thioamide; Amine; Aldehyde; Aqueous solvent.Abstract
Thioamides have been widely used in the fields of medicine and organic chemistry, some of which are essential bioactive compounds, plant protection agents, and drugs. It could also be used as a vulcanizing agent, an additive to lubricants and greases, and a ligand in organic synthesis. Usually, thioamide is synthesized at high temperatures or in the microwave using an expensive noble metal complex as catalysts. This paper presented a straightforward method for synthesizing thioamides by using N-tert-butylsulfinyl amide, aldehyde, and sulfur. The reaction was carried out in water, which is an environmentally friendly solvent. The reaction selectivity and yield were up to 89%.
References
[1]. Mahanta, N., Szantai-Kis, D. M., Petersson, E. J. Mitchell, D. A., "Biosynthesis and Chemical Applications of Thioamides", ACS Chem Biol., 14(2) (2019), pp. 142 - 163.
[2]. Jagodziński, T. S, "Thioamides as Useful Synthons in the Synthesis of Heterocycles", Chemical Reviews, 103(1) (2003), pp. 197 - 228.
[3]. Downer, N. K. Jackson, Y. A., "Synthesis of benzothiazoles via ipso substitution of ortho-methoxythiobenzamides", Org Biomol Chem., 2(20) (2004), pp. 3039 - 3043.
[4]. Jain, P., Verma, P., Xia, G., & Yu, J.-Q. “Enantioselective amine α-functionalization via palladium-catalysed C–H arylation of thioamides”. Nature Chemistry, 9(2) (2016), pp.140–144
[5]. Pathare, Sagar P., Chaudhari, Pramod S. Akamanchi, Krishnacharya G., "Sulfated tungstate: An efficient catalyst for synthesis of thioamides via Kindler reaction", Applied Catalysis A: General, 425-426 (2012), pp. 125-129.
[6]. Pribbenow, D. L. Bolm, C., "Recent advances in the Willgerodt-Kindler reaction", Chem Soc Rev., 42(19) (2013), pp. 7870-80.
[7]. Larik, F. A., Saeed, A., Muqadar, U., & Channar, P. A. “Application of Lawesson’s reagent in the synthesis of sulfur-containing medicinally significant natural alkaloids”, Journal of Sulfur Chemistry, 38(2) (2016), pp. 206–227.
