Regioselective Syntheses of Bis(indazolyl)methane Isomers: Controlling Kinetics and Thermodynamics via Tunable Non-Innocent Amines.

ABSTRACT: The selective synthesis of regioisomers from ambident N-heterocycles remains a challenge in organic chemistry. We report a general and modular method for the regioselective syntheses of bis-(indazolyl)-methane isomers, in which the outcome is controlled by the nature of the base. Specifically, we employed structurally diverse amines as noninnocent bases, whose steric and electronic propertiesparticularly their pK _aH and ability to act as methylene carriers or activatorsplay a decisive role in directing product distribution. By fine-tuning the amine structure, we achieved selective access to symmetrical and unsymmetrical isomers under mild, one-step conditions, without intermediate isolation. The use of amines over conventional inorganic bases was essential to enable bot

SUBMITTER: Alvarez-Sanchez M 

PROVIDER: S-EPMC12658713 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature