Base-Controlled Regiospecific Mono-Benzylation/Allylation and Diallylation of 4-Aryl-5-indolyl-1,2,4-triazole-3-thione: Thio-Aza Allyl Rearrangement

The regiospecific S-benzylation/allylation of two 4-aryl-5-indolyl-1,2,4-triazole-3-thione precursors was carried out using Et3N as a base. Allyl group migration from exocyclic sulfur to the triazole nitrogen (N3) successfully achieved in short time via thermal fusion without need for any catalyst. allylation indole nitrogen, along with or (N3), K2CO3 stronger S,N-Diallylated products were converted N,N-diallylated analogues simple approach. Structural analyses newly synthesized hybrids 2b and 5b investigated X-ray diffraction single crystal combined Hirshfeld calculations. compound crystallized monoclinic system P21/c space group, whereas 2b, comprises less symmetric triclinic P − 1 group. asymmetric unit contains one molecules respectively, while cell four both cases. analysis performed systems analyze non-covalent interactions that control molecular packing. For 5b, C…H, N…H, S…H, Cl…N H…H are most significant. Their percentages 23.7, 8.8, 4.5, 1.2 48.2, respectively. In case Cl…C, S…N, N…H have upper hand unit, these contacts 2.3, 0.9, 26.8, 38.7 9.3%, other corresponding values 4.4, 1.3, 22.1, 43.6 9.0%,