Influence of temperature for the azide displacement in benzodiazepine derivatives: Experimental and DFT study of competing SN1, SN2 and double SN2 reaction pathways

Molecules carrying the azido functionality are widely used as intermediates in medicinal chemistry. Pyrrolobenzodiazepines molecules with a broad range of interesting pharmacological properties. Due to wide importance azido-PBD key intermediate many synthetic pathways, this work we have investigated effect variety experimental parameters on mechanism nucleophilic substitution reaction for introducing an azide group into PBD scaffold. This study was carried out by combined and DFT approaches, showing that SN2 double pathways possible highly dependent temperature.