2-Bromo-, 2-chloro-, and 2-fluoro-pyridines, whose nucleophilicities are not high enough for them to attack dimethyl acetylenedicarboxylate at atmospheric pressure, react with the latter under high-pressure (10 kbar) at room temperature to give 1 : 2 adducts (from the bromo- and chloro-pyridines)(9aH- and 4H-quinolizines) or a 1 : 3 adduct (from the fluoro-pyridine).
K. Matsumoto, Y. Ikemi-Kono and T. Uchida, J. Chem. Soc., Chem. Commun., 1978, 543 DOI: 10.1039/C39780000543
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