Molecular Armatures. Synthesis and Structure of Troegers Base Analogues Derived from 4-, 2,4-, 3,4-, and 2,4,5-Substituted Aniline Derivatives

Article abstract of DOI:10.1021/jo00236a020

The preparation of biomimetic systems designed to mimic natural receptor sites and enzymic active sites requires the development of new synthetic strategies for preparing large molecules with predictable and well-defined shapes.In this paper a number of derivatives of 6H,12H-5,11-methanodibenzo<1,5>diazocines are prepared.The scope and limitations of the reaction of formaldehyde with aniline derivatives are examined.The molecules prepared have potential value as conformationally restricted armatures for the construction of biomimetic molecular systems.A crystallographic study reveals that the molecules are folded and that the angle formed by the two aryl rings ranges from 88 deg to 104 deg.Sulfonamides, bromides, alcohols, and amines can be introduced as side-chain substituents in these systems.