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 Apr. 2019
Accepted
06 Jūn. 2019
First published
06 Jūn. 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

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