Base-Mediated Synthesis of Imidazole-Fused 1,4-Benzoxazepines via 7-<i>exo-dig</i> Cyclizations: Propargyl Group Transformation.

ABSTRACT: Herein, we describe the synthesis of a series of imidazole-fused 1,4-benzoxazepines using 7-exo-dig cyclizations. Two sets of substrates, one containing disubstituted alkyne functional groups and the other featuring terminal alkynes, were synthesized by using O-propargylation, Sonogashira cross-coupling, and condensation reactions between aldehydes and o-diaminobenzene. While the disubstituted substrates yielded exocyclic E/Z configured cyclization products smoothly, the reactions involving terminal alkynes resulted in the formation of isomeric products with altered skeletal structures, in addition to the expected 7-exo-dig cyclization products. Density functional theory (DFT) calculations were used to clarify the mechanisms underlying the formatio

SUBMITTER: Korkmaz Cokol N 

PROVIDER: S-EPMC11976854 | biostudies-literature | 2025 Apr

REPOSITORIES: biostudies-literature