Abstract
Bis(alkylsulfanyl) derivatives of 1,2,5-thiadiazoles fused with aromatic and heteroaromatic rings containing long alkyl chains are of interest as compounds with liquid crystalline properties. In this communication, 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 was obtained from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 by a combination of two reactions—aromatic nucleophilic substitution SNAr and Buchwald–Hartwig cross-coupling. The structure of the newly synthesized compounds was established by means of elemental analysis; high-resolution mass spectrometry; 1H, 13C NMR, IR and UV spectroscopy; and mass spectrometry.
Highlights
Published: 25 October 2021Bis(alkylsulfanyl) derivatives of heteroaromatic compounds containing long alkyl chain are of interest as compounds with device applications
4,7-bis(dodecylthio)[1,2,5]thiadiazolo[3,4-d]pyridazine possesses liquid crystalline properties [1]; 4,7-bis(alkylthio)benzo[c][1,2,5]thiadiazole has been used as a precursor for discotic liquid crystals for device application in vertical electrode configuration [2]; and octa(alkylthio)substituted zinc phthalocyanines have been used as photosensitizers for photodynamic therapy [3]
Results and Discussion with regard to jurisdictional claims in Aromatic nucleophilic substitution of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with thiols led to the formation of 4,7-bis-thiosubstituted [1,2,5]thiadiazolo[3,4-d]pyridazines [4]; all attempts to isolate mono-substituted derivatives were unsuccessful
Summary
Bis(alkylsulfanyl) derivatives of heteroaromatic compounds containing long alkyl chain are of interest as compounds with device applications. We report the two-step synthesis of 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2. For the synthesis of 4,7-bis(alkylthio)benzo[c][1,2,5]thiadiazole, Buchwald–Hartwig conditions are required: treatment with alkylthiols and a mixture of Pd2 (dba)3 , DPPF, and DIPEA [2]. We assumed that the synthesis of 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 can proceed smoothly through a combination of the two reactions—nucleophilic substitution and Buchwald–Hartwig cross-coupling.
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