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Issue 26, 2019
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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

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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

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Article information


Submitted
11 Apr 2019
Accepted
06 Jun 2019
First published
06 Jun 2019

New J. Chem., 2019,43, 10491-10500
Article type
Paper

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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