Indole-based heterocyclic scaffolds have become increasingly important in medicinal chemistry due to their notable pharmacological and biological properties. Their role in the discovery and development of innovative drugs for treating various diseases highlights their value. This study aimed to synthesize C3-indole derivatives linked to various heterocyclic scaffolds, including thiophenes, thiazolidine-4-ones, and 1,3,4-thiadiazoles, via the reaction of ethylthioacetanilide 2 with different α-haloketones.The structures of the target compounds were established using