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Synthesis of new-type 1,3,6-triazocine via intramolecular reactions of iodocyclization and [3+2] azido cycloaddition

J. Heterocycl. Chem. 2020, 57(8), 3202‑3212

DOI: 10.1002/jhet.4028

Vaskevych R.; Vaskevych A.; Rusanov E.; Mel'nyk O.; Vovk M.

Selective iodocyclization of 6-(alkenylamino)-1-allylpyrazolo[3,4-d]pyrimidines provided hydrogenated derivatives of 1-allyl-8(9)-iodomethylimidazo(pyrimido)[1,2-a]pyrazolo[4,3-e]pyrimidines which were further reacted with NaN3 at 75°С to 80°С to give a series of new-type 1,3,6-triazocines annulated with the pyrazole, pyrimidine, imidazole (or pyrimidine), and 1,2,3-triazole rings. The compounds synthesized were structurally characterized by analytical, spectral (IR, 1H and 13C NMR, HPLC-mass), and X-ray diffraction data.

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