Synthesis, Structure, and Biological Activity of [2.2]Paracyclophane Derivatives. 8. α-Pyridyl([2.2]paracyclophan-4-yl)-phenylmethanol: Structure of the Complex with Cu(II) Chloride and Intramolecular Cyclization

Abstract

The reaction of 2-benzoylpyridine with 4-([2.2]paracyclophanyl)lithium or of 4-benzoyl[2.2]paracyclophane with 2-pyridyllithium gave α-pyridyl([2.2]paracyclophan-4- yl)phenylmethanol. X-ray analysis has been used to study the molecular and crystalline structure of its complex with Cu(II) chloride. It was found that this triaryl-substituted methanol undergoes an intramolecular cyclocondensation in refluxing formic acid and involves the pyridine ring and the cyclophane substituent. Heterocyclization at the ortho-position of the latter gives 10-phenyl[2.2]paracyclophano[4,5-b]indolizine and cyclization at the pseudo-gem-position the 1-phenyl-1,1a-dehydro-6-aza[3.2.2](1,2,5)-6H-cyclophano[1,2-a]pyridine. The compounds prepared have luminescent properties.