Synthesis of α,β′- and β,β′-Linked Dimethoxycarbonyldipyrromethanes by Rothemund-Type Condensation

• Published in: Synlett 2012-07, Vol.23 (12), p.1835-1839
• Main Authors: Journot, Guillaume, Stoeckli-Evans, Helen, Neier, Reinhard
• Format: Article
• Language: English
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; letter; Organic chemistry; Preparations and properties
• ISSN: 0936-5214; 1437-2096
• DOI: 10.1055/s-0032-1316538

Abstract The Rothemund-type condensation of methoxycarbonylpyrrole with acetone produces mainly the α,β′-linked dipyrromethane, a building block for the synthesis of N-confused macrocycles. The influence of the reaction conditions on the regioselectivity of the process is reported. The X-ray structures of the α,α′-, α,β′- and β,β′-linked dipyrromethanes show an interesting discrimination of the structurally different types of hydrogen bonds.