7-Bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one

Timofey N Chmovzh,Oleg A Rakitin

doi:10.3390/m1229

Timofey N Chmovzh, Oleg A Rakitin

Open Access

https://doi.org/10.3390/m1229

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Abstract

New heterocyclic systems containing 1,2,5-chalcogenadiazoles are of great interest for the creation of organic photovoltaic materials and biologically active compounds. In this communication, 3,6-dibromopyridazine-4,5-diamine was investigated in reaction with selenium dioxide in order to obtain 4,7-dibromo-[1,2,5]selenadiazolo[3,4-d]pyridazine. We found that 7-bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)-one, the first representative of the new heterocyclic system, was isolated as a hydrolysis product of the corresponding 4,7-dibromoderivative. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy, and mass spectrometry.

Highlights

Ortho-Diamine moiety in benzene or heterocyclic rings is often used for the construction of fused 1,2,5-chalcogena diazoles [1,2,3,4], which are of great interest as various photovoltaic materials, i.e., organic solar cells (OSCs), organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and others [5,6,7,8,9,10]. 4,7-Dibromo derivatives of these heterocyclic systems are the most convenient precursors for the synthesis of photoactive materials [11]
We report on the study of the reaction between 3,6-dibromopyridazine-4,5-diamine
It was found that the treatment of 3,6-dibromopyridazine-4,5-diamine 1 with SeO2 in EtOH under reflux after 1 h led to the formation of 7-bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin-4(5H)one 2 in good yield (Table 1, Entry 1)

Summary

Introduction

Ortho-Diamine moiety in benzene or heterocyclic rings is often used for the construction of fused 1,2,5-chalcogena (thia, selena, tellura) diazoles [1,2,3,4], which are of great interest as various photovoltaic materials, i.e., organic solar cells (OSCs), organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and others [5,6,7,8,9,10]. 4,7-Dibromo derivatives of these heterocyclic systems are the most convenient precursors for the synthesis of photoactive materials [11]. Ortho-Diamine moiety in benzene or heterocyclic rings is often used for the construction of fused 1,2,5-chalcogena (thia, selena, tellura) diazoles [1,2,3,4], which are of great interest as various photovoltaic materials, i.e., organic solar cells (OSCs), organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and others [5,6,7,8,9,10]. 4,7-Dibromo derivatives of these heterocyclic systems are the most convenient precursors for the synthesis of photoactive materials [11]. We synthesized one of the interesting precursors for fused 1,2,5-chalcogenadiazolopyridazines—3,6-dibromopyridazine-4,5-diamine 1 [12]. We report on the study of the reaction between 3,6-dibromopyridazine-4,5-diamine. 1 and selenium dioxide and the synthesis of 7-bromo-[1,2,5]selenadiazolo[3,4-d]pyridazin4(5H)-one 2, the first representative of a new heterocyclic system

Results and Discussion

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Materials and Methods