This review highlights ortho-alkynyl quinone methides as versatile intermediates for heterocycle synthesis, suggesting their increasing importance in organic chemistry.
Ortho-alkynyl quinone methides (o-AQMs) are valuable building blocks in organic synthesis, featuring a unique hybrid structure that combines an alkyne with an ortho-quinone methide (o-QM) unit. This architecture results in a synergistic interplay of reactivities: the alkyne moiety participates in addition and cyclization reactions, while the o-QM unit is prone to nucleophilic addition and redox transformations. Such dual functionality renders o-AQMs highly versatile as reactive intermediates for constructing polycyclic frameworks, especially oxygen-containing heterocycles like furans and pyrans. This review summarizes the physicochemical properties, synthetic methods, and applications of o-AQMs as privileged intermediates. It provides a comprehensive overview of the current state and emerging trends in utilizing o-AQMs for heterocycle synthesis, highlighting their growing potential to advance synthetic chemistry.
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Liu et al. (2026) studied this question.
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