Article
Influence of temperature for the azide displacement in benzodiazepine derivatives: Experimental and DFT study of competing SN1, SN2 and double SN2 reaction pathways
Registro en:
EVANGELISTA, Tereza Cristina Santos et al. Influence of temperature for the azide displacement in benzodiazepine derivatives: Experimental and DFT study of competing SN1, SN2 and double SN2 reaction pathways. Tetrahedron Letters, v. 68, 152937, 5 p, Feb. 2021.
0040-4039
10.1016/j.tetlet.2021.152937
Autor
Evangelista, Tereza Cristina Santos
Delarmelina, Maicon
Addla, Dinesh
Allão, Rafael A.
Kaiser, Carlos Roland
Carneiro, José Walkimar de M.
Silva Jr., Floriano Paes
Ferreira, Sabrina Baptista
Resumen
Molecules carrying the azido functionality are widely used as intermediates in medicinal chemistry.
Pyrrolobenzodiazepines are molecules with a broad range of interesting pharmacological properties.
Due to the wide importance of azido-PBD as a key intermediate in many synthetic pathways, in this work
we have investigated the effect of a variety of experimental parameters on the mechanism of nucleophilic
substitution reaction for introducing an azide group into the PBD scaffold. This study was carried out by
combined experimental and DFT approaches, showing that SN2 and double SN2 pathways are possible
and highly dependent on the reaction temperature.