Issue 26, 2019

On the nucleophilic derivatization of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine: basis for biologically interesting species and building blocks for organic materials

Abstract

Delving into the scarcely explored versatility and selectivity of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine towards aromatic nucleophilic substitution, eleven new compounds were synthesized using different nucleophiles (alcohols, amines, and thiols). The compounds described herein allow us to get a glimpse of important building blocks for the synthesis of biologically attractive molecules and for organic materials or species with fluorescence properties. Given the structural diversity of the electron-donating substituents, the effect of the functional groups introduced was studied through a tandem experimental-theoretical approach to analyze the electronic properties bestowed on the TDAP core. Insights into the selectivity towards a single position and the differences between nucleophiles were achieved through a DFT analysis of the energetics of the reactions performed.

Graphical abstract: On the nucleophilic derivatization of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine: basis for biologically interesting species and building blocks for organic materials

Supplementary files

Article information

Article type
Paper
Submitted
11 abr. 2019
Accepted
06 jun. 2019
First published
06 jun. 2019

New J. Chem., 2019,43, 10491-10500

On the nucleophilic derivatization of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine: basis for biologically interesting species and building blocks for organic materials

O. González-Antonio, M. Navarro Villalobos, M. M. Vázquez-Alvarado, R. Santillan, B. Flores-Pérez, M. Romero-Ávila and N. Farfán, New J. Chem., 2019, 43, 10491 DOI: 10.1039/C9NJ01855G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements