Pyridyne

[1] Pyridynes are the class of reactive intermediates derived from pyridine.

[3] In 1969 Zoltewicz and Nisi trapped 3,4-pyridyne in a reaction of 3-bromopyridine with methylmercaptan and sodium amide in ammonia.

[4] In 1972 Kramer and Berry inferred the formation of 3,4-pyridyne in gas-phase photolysis of pyridine-3-diazonium-4-carboxylate via time-of-flight mass spectrometry.

[5] In 1988 Nam and Leroy reported the matrix isolation (13K, Ar) of 3,4-pyridyne by photolysis of 3,4-pyridinedicarboxylic anhydride with the IR-spectrum revealing an acetylenic bond in the same way as ortho-benzyne.

Strategies involving pyridynes have been employed in the total syntheses of ellipticine[6][7] and (S)-Macrostomine.