Reactivity of 2-substituted 3-ethylsulfonylpyridines
(1997) Societes Chimiques Belges. Bulletin — Vol. 106, n° 3, p. 151-157 (1997)
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- 2-Chloro-3-ethylsulfonylpyridine 6 was transformed by acidic or basic hydrolysis into 2-hydroxy-3-ethylsulfonylpyridine 4, which was in the OH form, i.e. without the 2-pyridone isomer. Diazomethane however transformed 4 into the mixture of the N- and O-methyl derivatives. Sodium sulfite reaction with 6 generated 2-sodiumsulfonate-3-ethylsulfonylpyridine 7. This did not react with SOCl2, and PCl5 transformed it into 6, no 2-sulfonylchloridepyridine being isolated. Potassium phthalimide reaction with 6 gave 2-phthaiimido-3- ethylsulfonylpyridine 8', which was transformed by hydrazine into 2-amino-3-ethylsulfonylpyridine 8. This was not transformed by heating in acidic or basic aqueous solutions. In dilute acid solution, sodium nitrite transformed 8 into 4. in concentrated hydrochloric acid, the diazonium salt of 8 however was not formed. 2(N-(4,6-Dimethoxy)pyrimidin-2-yl)amino-3-ethylsulfonylpyridine 3 in concentrated hydrochloric acid was transformed into 8, the intermediate N-(3-ethylsulfonyl-pyridine-2-yl)-guanidine 9 being isolated when the heating time was shorter.
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Rouchaud, J., Neus, O., & Moulard, C. (1997). Reactivity of 2-substituted 3-ethylsulfonylpyridines. Societes Chimiques Belges. Bulletin, 106(3), 151-157. https://hdl.handle.net/2078.5/42440 (Original work published 1997)