Thiophenes are a high class in heterocyclic chemistry, they are versatile compounds with a wide range of applications in chemistry, pharmaceutical, and advanced materials due to their stable structure and unique properties. Among these, 2-substituted thiophenes, such as 2-acetylthiophene and thiophene-2-carbaldehyde, stand out as chemical compounds of particular interest for scientific research. These compounds serve as crucial scaffolds in the synthesis of new bioactive polyheterocycles due to the presence of the ketone or aldehyde function, which allows them to react with other compounds. Our research team has extensive experience in the synthesis of variously substituted thiophenes. In our research, we established a rapid, efficient, and environmentally friendly procedure to synthesize a new series of heterocycles containing sulfur and nitrogen. The first step involves the chloroformylation of commercial ketones into β-chloroacroleins via the Vilsmeier-Haack reaction, well-known in organic chemistry for their wide application in organic synthesis, followed by a two-step cyclization process to obtain 2-acetylthiophene in moderate yields. This 2-acetylthiophene is then used to prepare new polyheterocyclic compounds, particularly of the bis-thiophenes and thieno-pyrroles types.This innovative approach not only improves the efficiency of synthesizing these complex molecules but also opens new possibilities for the development of bioactive compounds with potential applications in various fields.