Synlett 2012; 23(12): 1835-1839
DOI: 10.1055/s-0032-1316538
letter
© Georg Thieme Verlag Stuttgart · New York

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

Guillaume Journot
a  Institut de chimie, Université de Neuchâtel, Avenue Bellevaux 51, 2000 Neuchatel, Switzerland, Fax: +41(32)7182428   Email: Reinhard.Neier@unine.ch
,
Helen Stoeckli-Evans
b  Institut de physique, Université de Neuchâtel, Avenue Bellevaux 51, 2000 Neuchatel, Switzerland
,
Reinhard Neier*
a  Institut de chimie, Université de Neuchâtel, Avenue Bellevaux 51, 2000 Neuchatel, Switzerland, Fax: +41(32)7182428   Email: Reinhard.Neier@unine.ch
› Author Affiliations
Further Information

Publication History

Received: 07 February 2012

Accepted after revision: 22 May 2012

Publication Date:
29 June 2012 (online)


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.

Supporting Information

 
  • References and Notes

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  • 9 Reactions monitored by GC
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