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A novel alkyne-assisted annulation reaction of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones is reported, providing a facile synthesis of substituted 2H-pyrans in good yields. This reaction divulges the inimitable reactivity of the MBH-carbonates of propiolaldehydes as C3-synthons wherein the alkyne functionality promoted the reaction without participating in the oxa-[3+3] annulation. The obtained products, having alkyne and ester functionalities, allowed further annulations to generate diverse pyrano[3,4-c]pyran-1-ones.