Synthetic procedure to pyrido[2,1-f][1,2,4]triazinium salt and related compounds |
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Authors: | Sándor Bátori Dorottya Csányi Daniella Takács Orsolya Egyed Zsuzsanna Riedl György Hajós |
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Institution: | 1. Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117 Budapest, Magyar tudósok körútja 2 Hungary;2. NMR Research Laboratory of Instrumentation Centre, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117 Budapest, Magyar tudósok körútja 2 Hungary |
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Abstract: | N-aminopyridyl ketone salts were reacted with formamide to yield heteroaromatic pyrido2,1-f]1,2,4]triazinium salts. Upon storage of these products in the presence of water, formation of covalent hydrates have been observed. Reaction of the same starting compound with urethane yielded 3-chloropyrido2,1-f]1,2,4]triazinium salt which readily reacted with secondary amines to afford 3-amino derivatives. An analogous ring closure reaction of 2-formylaminomethyl- and formaminobenzylpyridine allowed the synthesis of the partially reduced 3,4-dihydropyrido2,1-f]1,2,4]triazinium compounds. The cyclization procedure was also applied for the synthesis of the related pyrimido2,1-f]1,2,4]triazinium salt. |
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Keywords: | Ring closure Zwitterion Heteroaromatic Fused triazinium salt Covalent hydrate |
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