Direction of the Primary Nucleophilic Attack in the Kost—Sagitullin Rearrangement.

Recyclization of intermediates in an enamine rearrangement of a pyrimidinium salt when treated with isoniazide

“…The synthesis of compound 6 [R f 0.63 (i-PrOH-ammonia, 1:1)] is described in [3], and its melting point and 1 H and 13 C NMR spectra, as for compounds 8 [R f 0.52 (toluene-acetone, 1:2)] and 9 [R f 0.67 (tolueneacetone, 1:1)] [4,5], are the same as for a known sample.…”

Kost-Sagitullin Rearrangement and Other Isomerization Recyclizations of Pyrimidines. (Review)

“…Experimental evidence for the possibility of attack by the nucleophile at position 2 was obtained during the reaction (in the cold) of the pyrimidinium salt 25 with an alcohol solution of potassium hydroxide; the intermediate compound 51, the structure of which was confirmed by NMR, IR, and mass spectrometry, was isolated [101]. …”