• Media type: E-Article
  • Title: Synthesis of Pyrrolo[2,3‐d]pyrimidines by Copper‐Mediated Carbomagnesiations of N‐Sulfonyl Ynamides and Application to the Preparation of Rigidin A and a 7‐Azaserotonin Derivative
  • Contributor: Nickel, Johannes; Fernández, Maitane; Klier, Lydia; Knochel, Paul
  • imprint: Wiley, 2016
  • Published in: Chemistry – A European Journal
  • Language: English
  • DOI: 10.1002/chem.201602519
  • ISSN: 0947-6539; 1521-3765
  • Keywords: General Chemistry ; Catalysis ; Organic Chemistry
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>The treatment of readily available <jats:italic>N</jats:italic>‐alkynyl‐5‐iodo‐6‐sulfamido‐pyrimidines with <jats:italic>i</jats:italic>PrMgCl⋅LiCl followed by a transmetalation with CuCN⋅2 LiCl produces, after intramolecular carbocupration, metalated py<jats:bold>r</jats:bold>rolo[2,3‐<jats:italic>d</jats:italic>]pyrimidines. Quenching of these pyrimidines with allylic halides or acid chlorides results in polyfunctional pyrrolo[2,3‐<jats:italic>d</jats:italic>]pyrimidines. Further reaction with ICl and a Negishi cross‐coupling, using PEPPSI‐<jats:italic>i</jats:italic>Pr as the catalyst, furnishes fully substituted N‐heterocycles. A formal synthesis of the marine alkaloid rigidin A has been achieved as well as the preparation of a derivative of 7‐azaserotonine, related to the natural hormone serotonin.</jats:p>