Multimolecular Self-Organization of 1-Acetyl-1,3-bis(haloarylamines) in KOH/DMSO System: From Acetylene Gas and o-Halo Arylamines toward a Higher Molecular Complexity and Diversity.

An unprecedented self-organization of three molecules of acetylene, two molecules of o-halo arylamine, and one molecule of water to 1-acetyl-1,3-bis(haloarylamines) in the KOH/DMSO system has been discovered. These high-value 1,3-bis(arylamines) are capable of acting as efficient "platform molecules" to provide one-pot access to hexahydropyrrolo[3,2-b]indoles, 3-haloarylamino-pyrrolidines, benzyliden piperidinols, and other functionalized diamines.