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Communication | Regular issue | Vol 14, No. 1, 1980, pp.19-22
Published online, 1st January, 1970
DOI: 10.3987/R-1980-01-0019
Reexamination of the Reaction of Pyridine 1-Oxide with Phenyl Isocyanate. The Isolation of 2,3-Dihydropyridine Intermediate and the Study on the Reaction Course

Takuzo Hisano,* Toshikazu Matsuoka, Masataka Ichikawa, and Masatomo Hamana*

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan


A 2,3-dihydropyridine (4a) was isolated from the reaction of pyridine 1-oxide (1a) with phenyl isocyanate (2) at 90° in DMF. Heating 4a at 110° in DMF gave 2-anilinopyridine (5a). The time course studies on the reactions of 1a and 2 demonstrated that the initially formed 1,2-dihydropyridine (3a) immediately rearranged to 4a, and 5a was formed not from 3a but from 4a.