1995
DOI: 10.1016/0040-4020(95)00474-m
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Recyclization of polysubstituted pyridinium salts

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Cited by 17 publications
(5 citation statements)
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“…The Kost-Sagitullin rearrangement was first discovered and studied under the leadership of Prof. A. N. Kost in derivatives of pyridine and pyrimidine [5,[64][65][66][67][68][69][70][71][72][73][74][75][76][77]. Such recyclizations were realized both in N-alkylazinium salts and in annelated azine systems containing a bridging nitrogen atom (common to the two heterocycles).…”
Section: Isomerization N-c Recyclization (The Kost-sagitullin Rearranmentioning
confidence: 99%
“…The Kost-Sagitullin rearrangement was first discovered and studied under the leadership of Prof. A. N. Kost in derivatives of pyridine and pyrimidine [5,[64][65][66][67][68][69][70][71][72][73][74][75][76][77]. Such recyclizations were realized both in N-alkylazinium salts and in annelated azine systems containing a bridging nitrogen atom (common to the two heterocycles).…”
Section: Isomerization N-c Recyclization (The Kost-sagitullin Rearranmentioning
confidence: 99%
“…Recyclization of the salt 1b occurs regiospecifically; the possible product of heterocyclization with participation of the cyano group [2,3] is not observed. The meta-terphenyls with substituents on one ring that we synthesized cannot be obtained by other known methods.…”
mentioning
confidence: 98%
“…Nicotinonitriles 1a-c were prepared by a rearrangement of 3,5-dicyanopyridinium salts upon treatment with sodium hydroxide. 19,20 The construction of a pyrazole ring in a fused ring system was done upon N-nitrosation of a secondary amino group in compounds 1a-c with sodium nitrite in acetic acid followed by the reduction of resulting N-nitrosoamines 2a-c † with zinc powder in acetic acid. During the reduction of the N-nitroso group of 2a-c to a substituted hydrazino group, intramolecular condensation onto acetyl group of pyridine ring simultaneously occurred and resulted in pyrazole ring closure to form 3a-c. ‡ All the reactions were performed under mild conditions and produced 2a-c and 3a-c in high yields.…”
mentioning
confidence: 99%