41813-97-2Relevant academic research and scientific papers
Regioselective microwave synthesis and derivatization of 1,5-diaryl-3-amino-1,2,4-triazoles and a study of their cholinesterase inhibition properties
Santos, Sabrina Neves,Alves De Souza, Gabriela,Pereira, Thiago Moreira,Franco, Daiana Portella,De Nigris Del Cistia, Catarina,Sant'anna, Carlos Mauricio R.,Lacerda, Renata Barbosa,Kümmerle, Arthur Eugen
, p. 20356 - 20369 (2019)
Herein we describe the development of an efficient one-pot regioselective synthesis protocol to obtain N-protected or N-deprotected 1,5-diaryl-3-amino-1,2,4-triazoles from N-acyl-N-Boc-carbamidothioates. This improved protocol using microwave irradiation and low reaction times (up to 1 h) furnished desired compounds in yields ranging from 50 to 84%. This chemistry is useful for a variety of aromatic groups with electronically diverse substituents. The design and correct derivation of the amino group led to compounds able to inhibit cholinesterases with good IC50 of up to 1 μM. Also, the mode of action (mixed-type) and SAR analysis for this series of compounds was described by means of kinetic and molecular modelling evaluations, showing potential for this class of compounds as new scaffolds for this biological activity.
Highly efficient cyanoimidation of aldehydes
Yin, Ping,Wen-Bo, Ma.,Chen, Yue,Huang, Wen-Cal,Deng, Yong,He, Ling
supporting information; experimental part, p. 5482 - 5485 (2010/02/27)
"Chemical Equation Presented" Cyanoimidation of aldehydes using cyanamide as a nitrogen source and using NBS as an oxidant was achieved in high yields without the addition of a catalyst. The method has several advantages, Including mild conditions, simple workflow, and inexpensive reagents. The reaction proceeds in a one-pot manner, giving rise to the formation of intermolecular C-N and C-O bonds. Subsequently, the substituted W-cyanobenimidate products may also undergo a cyclization reaction to give 1,2,4-triazole derivatives in high yields.
SYNTHESIS AND THERMOLYSIS OF SOME N-HYDROXIMOYL- AND N-HYDRAZONOYLAZOLES
Plenkiewicz, Jan,Zdrojewski, Tadeusz
, p. 675 - 710 (2007/10/02)
The reactions of nitrile oxides or nitrile imines with pyrazole, imidazole, 1,2,3- and 1,2,4-triazole or tetrazole derivatives yield the appropriate N-hydroximoyl- or N-hydrazonoylazoles.Thermolysis of 1-hydroximoyltetrazoles, depending on the nature of the substituents in the tetrazole ring, yields 1,2,4-oxadiazoles or 5-amino-1,2,4-oxadiazoles upon hydrazoic acid or nitrogen evolution.Under similar conditions, 1-hydrazonoyltetrazoles give 1,2,4-triazoles or 5-amino-1,2,4-triazoles while 2-hydrazonoyltetrazoles decompose to the dihydro-1,2,4,5-tetrazine derivatives.
