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1 article(s) from Shutalev, Anatoly D.

Unprecedented synthesis of a 14-membered hexaazamacrocycle

Anastasia A. Fesenko and
Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

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Scheme 1: Synthesis of the key intermediate of the macrocycle preparation, 3-[(ethoxymethylene)amino]-1-methy...

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Scheme 2: Synthesis of macrocycle 5 by the reaction of imidate 4 with hydrazine hydrate.

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Scheme 3: Plausible pathway for the transformation of imidate 4 into macrocycle 5.

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Scheme 4: Synthesis of pyrazolopyrimidine 8 by the reaction of imidate 4 with hydrazine hydrate.

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Scheme 5: Synthesis of macrocycle 5 by the dimerization of pyrazolopyrimidine 8.

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Scheme 6: Plausible pathway for the dimerization of pyrazolopyrimidine 8 into macrocycle 5.

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Figure 1: Gibbs free energy diagram (B3LYP/6-311++G(d,p)) for the N₂H₄-promoted transformation of pyrazolopyr...

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Scheme 7: Transformation of macrocycle 5 into pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine 13 and pyrazolo...

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Published 15 Nov 2023

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