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

• structure and reactivity of the obtained macrocycle are outlined. Keywords: amidrazones; hexaazamacrocycles; pyrazolo[3,4-d]pyrimidines; ring contraction; self-assembly; Introduction The chemistry of polyazamacrocycles (PAMs) is currently one of the most rapidly developing areas of heterocyclic chemistry

• prepared compounds were able to chelate various metal cations through the N1, N4, N8, and N11 atoms [37][38]. In continuation of our research on 1,2,4,8,9,11-hexaazamacrocycles, which are under-explored representatives of the PAMs family, we were particularly interested in the synthesis of more unsaturated

• and therefore more conformationally rigid compounds. Previously, the unintentional preparation of two polyunsaturated 1,2,4,8,9,11-hexaazamacrocycles fused with two benzene or two pyrazole rings has been reported [39][40]. In particular, Dolzhenko et al. attempted to reproduce the synthesis of 4-imino