Tetrahedron Letters p. 5065 - 5068 (1995)
Update date:2022-08-04
Topics:
Chou, Chin-Hsing
Wu, Cheng-Chang
Chen, Wey-Kao
The temperature and pressure dependence of products formed on pyrolysis of 3-chloroformyl-2-methylpyridine (6) have been studied.Pyrolysis of 6 at 575 deg C and ca. 1 x 10-4 torr gives pyridocyclobuten-5-one (5) in 20percent yield.Pyrolysis of 6 at 575 and 800 deg C and under the pressure of ca. 1 x 10-2 torr give 1-azafulvenallene (7, 46percent) and 1-cyanocyclopentadiene (8, 42percent), respectively.Irradiation of 5 (λ > 300 nm) in methanol affords 2-methoxy-3-acetylpyridine (9) quantitatively.
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