The presented research work demonstrates a new methodology for generating a petite library of novel flavonol derivatives via Algar-Flynn-Oyamada reaction. Amongst oxygen containing heterocycles, flavonoids are versatile scaffolds due to their manifestation as crucial components in various natural products and encompassing massive biological activities. Thus, in view of the immense significance of flavonols and the pronounced effect of microwave-assisted protocol, a systematic and efficient scheme is put together for constructing the target motive and its derivatives by both classical and novel method. Initially, 2-hydroxy chalcones are assembled through an innovative conventional technique, later followed by the formation of flavonols. This methodical protocol results in enhanced yield with reduced reaction times under benign and environmental friendly conditions.