Nickel, Johannes;
Fernández, Maitane;
Klier, Lydia;
Knochel, Paul
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
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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
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>