Sulfur-based energetic materials 3 to 7 were synthesized considering the limited availability of structural combinations of polynitrogen- and oxygen-based organic scaffolds, thereby advancing their limits. All of them were fully characterised using infrared spectroscopy (IR), multinuclear magnetic resonance spectroscopy (NMR), high-resolution mass spectrometry (HRMS), elemental analysis (EA), and differential scanning calorimetry (DSC) studies. Furthermore, the molecular structure of compound 3 was confirmed using single-crystal X-ray diffraction studies (SC-XRD). All compounds exhibited good density (1.68-1.81 g cm-3), moderate detonation performance (VOD = 5747-7075 m s-1; DP = 14.39-19.35 GPa), high thermal stability (159-246 °C) and insensitivity towards impact and friction stimuli (IS > 40 J and FS > 360 N). This is the first instance of an energetic alliance of pyrazine and thiadiazole frameworks, which can be considered as a developmental step in the field of energetic materials.