- Unusually Facile Ring-Opening Reaction in the Pyridine System
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Reaction of 2-acetylpyridine with methyl 1-methylhydrazinecarbodithioate (2) resulted in formation of methyl (E,Z,E)-methylhydrazinecarbodithioate (4b) rather than the expected hydrazone, 3b.Reaction of pyridine-2-carboxaldehyde with 2, however, gave mostly the corresponding hydrazone 3a and some triazine 4a.Alkylation of 4a and 4b with iodomethane afforded the 3-methylthio derivatives 8a and 8b, respectively.The structure of 8a was determined by 1H NMR spectrometry and confirmed by a single-crystal X-ray analysis.Reaction of hydrazone 3b with 2 gave 4b, while treatment of 3b with dimethylamine afforded 6-(dimethylamino)-3,6-dihydro-1,3-dimethyl-4H-pyrido-triazine-4-thione (14a).Alkylation of 14a with iodomethane in aqueous base resulted in the formation of (Z,E)-4--2-butenal (15).Reaction of aldehyde 15 with 2 gave 4b.
- Scovill, John P.,Silverton, J.V.
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p. 4372 - 4376
(2007/10/02)
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