In this study, we report the development of efficient synthetic strategies for the preparation of novel 2'-carboxyl isoflavones and their recyclization products, pyrazoles and oxazoles. Utilizing readily accessible starting materials and mild reaction conditions, the synthesis affords valuable compounds with good to excellent yields. The presence of diverse functional groups, including hydroxyl, carboxyl, and carboxamido moieties, renders these molecules attractive for biological screening and targeted structural modifications. This work unveils new avenues for the design of compounds exhibiting a wide range of beneficial properties and opens new opportunities for future research into intramolecular interactions of proximal functional groups.