38385-51-2Relevant academic research and scientific papers
A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water
Chakraborti, Gargi,Dash, Jyotirmayee,Mandal, Tirtha,Roy, Charles Patriot
supporting information, p. 7970 - 7973 (2021/08/17)
A cascade sequence involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazolesviathe regioselective formation ofN2-carboxyalkylated triazoles. The reaction proceeds in aqueous media through intriguing reaction kinetics using a CuI-prolinamide catalyst system. Prolinamide promotes the novel organocatalytic 1,2-acyl migration as well as hydrolysis of the resultingN2-carboxyalkylated triazoles.
A flow strategy for the rapid, safe and scalable synthesis of N-H 1, 2, 3-triazoles via acetic acid mediated cycloaddition between nitroalkene and NaN3
Li, Dong,Liu, Lei,Tian, Yu,Ai, Yongjian,Tang, Zhike,Sun, Hong-bin,Zhang, Gang
, p. 3959 - 3965 (2017/06/13)
The N-unsubstituted 4-aryl-1H-1,2,3-triazoles were synthesized via the acetic acid promoted cycloaddition between β-nitrostyrenes with sodium azide under transition-metal-free conditions in a continuous flow microreactor. The continuous-flow microreactor provided a safe environment for the dangerous reagents NaN3 and nitroalkene, and offered such a rapid procedure that the triazoles were formed in less than 4 min. In addition, the excess sodium azide was quenched by the by-product HNO2 in the presence of acetic acid. The scale-up experiment proved again that the yield did not drop in the flow reaction. Moreover, the synthesis of N-unsubstituted 1,2,3-triazole was also explored via a one pot reaction with aldehyde, nitromethane and sodium azide, and this reaction was monitored with an “in-tube retention time gradient” (IT-RTG) technology, which may be a novel application of the continuous-flow microreactor.
1,2,3-Triazoles as conjugative π-linkers in push-pull chromophores: Importance of substituent positioning on intramolecular charge-transfer
Jarowski, Peter D.,Wu, Yi-Lin,Schweizer, W. Bernd,Diederich, Francois
supporting information; experimental part, p. 3347 - 3350 (2009/05/11)
(Chemical Equation Presented) Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from λmax = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.
