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

Evangelista, Tereza Cristina Santos, Delarmelina, Maicon, Addla, Dinesh, Allão, Rafael A., Kaiser, Carlos Roland, Carneiro, José Walkimar de M., Silva-Jr, Floriano Paes and Ferreira, Sabrina Baptista 2021. 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 68 , 152937. 10.1016/j.tetlet.2021.152937

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Abstract

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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Date of First Compliant Deposit: 10 March 2021
Date of Acceptance: 11 February 2021
Last Modified: 23 Feb 2022 17:04
URI: https://orca.cardiff.ac.uk/id/eprint/139369

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