423157-61-3Relevant academic research and scientific papers
On the development of a nucleophilic methylthiolation methodology
Carvalho, Bernardo Basbaum Portinho De Puga,Amaral, Adriane Antonia Pereira,De Castro, Pedro P?ssa,Ferreira, Fernanda Cerqueira Moreira,Horta, Bruno Araújo Cautiero,Amarante, Giovanni Wilson
, p. 5420 - 5426 (2020/08/03)
Methylthiolation reactions are usually explored to access organosulfur compounds using methanethiol, an extremely flammable and toxic compound. Herein, methylthiomethyl esters were successfully applied as novel methylthiolation reagents in a low cost, transition-metal-free methodology. These reagents allowed the methylthiolation of a wide scope of chalcones, acyl ester derivatives and Morita-Baylis-Hillman acetates with good group tolerance, affording the methylthiolated products in moderate to excellent yields. The reaction mechanism was investigated through several control experiments, as well as by theoretical calculations employing Density Functional Theory. The results strongly support that a sulfurane and a sulfonium ylide appear as key intermediates and that a Pummerer type rearrangement is also crucial for the formation of this novel reagent. Furthermore, the methylthiolation mechanism is likely to proceed through the nucleophilic attack of the reagent, followed by an entropically favoured step involving the acetate attack to the positively charged species, then releasing the product. This journal is
Synthesis of substituted 3-methylene-2-pyridones from Baylis-Hillman derivatives and its application for the generation of 2-pyridone substituted spiroisoxazolines
Singh, Virender,Yadav, Gaya P.,Maulik, Prakas R.,Batra, Sanjay
, p. 2979 - 2991 (2008/09/19)
The synthesis of substituted 3-methylene-2-pyridones via SN2 displacement reaction of nucleophiles bearing a keto group on the acetyl derivative of Baylis-Hillman adducts of acrylonitrile followed by TFA/H2SO4-mediated int
Synthesis and antibacterial evaluation of ureides of Baylis-Hillman derivatives
Nag, Somnath,Pathak, Richa,Kumar, Manish,Shukla,Batra, Sanjay
, p. 3824 - 3828 (2007/10/03)
The synthesis of several 1-(2-cyano-3-aryl-allyl)-3-aryl-urea(thiourea) constructed from the reaction between allylamines generated from Baylis-Hillman acetates and substituted isocyanates and isothiocyanates has been described. Further, their cyclization in the presence of a base led to the formation of 5-arylmethyl-4-imino-3-aryl-3,4-dihydro-1H-pyrimidin-2-ones. All compounds were tested for their antibacterial activity. Few of the compounds showed superior activity or were equipotent to the standard antibacterial agents.
