Coro Julieta, Alvarez-Puebla Ramon, Montero Ana L, Suárez Margarita, Martin Nazario, Perez-Pineiro Rolando
Laboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana, 10400, Ciudad Habana, Cuba.
J Mol Model. 2008 Jul;14(7):641-7. doi: 10.1007/s00894-008-0314-z. Epub 2008 May 17.
Based on experimental evidence and DFT studies, a probable cyclization route to 1,3,5-thiadiazinanes-2-thiones in aqueous medium is proposed. Experimental facts suggest the formation of a {[hydroxymethyl (substituted) carbamothioyl] sulfanyl}methanol intermediate via reaction of dithiocarbamate (DTC) and formaldehyde. Nucleophilic addition of glycine to this intermediate generates an adduct that undergoes intramolecular heterocyclization via an S(N)2 reaction. Computational calculations predict an active role of water in the reaction mechanism that promotes intramolecular cyclization.
基于实验证据和密度泛函理论（DFT）研究，提出了在水介质中形成1,3,5-噻二嗪烷-2-硫酮的一种可能的环化途径。实验事实表明，通过二硫代氨基甲酸盐（DTC）与甲醛反应形成{[羟甲基（取代）氨基硫甲酰基]硫烷基}甲醇中间体。甘氨酸对该中间体的亲核加成产生一种加合物，该加合物通过S(N)2反应进行分子内环化。计算预测水在促进分子内环化的反应机理中起积极作用。
