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Given the attractive ability of 2-oxoaldehyde/ 2-oxoiminium ions to functionalize molecules directly at ostensibly unreactive positions, the reactivity of aldehydic group/ iminium ions having -CH2 group replaced by C=O is explored. Background studies on 2-oxo-driven unconventional reactions and the ability of 2-oxoiminium cations to promote reactions via an iminium-catalyzed or iminium-equivalent pathway are apparently unavailable. At this junction, we further envisaged that difference in activation of 2-oxoaldehydes and 2-oxoiminium cations lead us to develop new directions in 2-oxo driven novel chemistry