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Nickel, Johannes; Fernández, Maitane; Klier, Lydia; Knochel, Paul (2016): 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. In: Chemistry-A European Journal, Vol. 22, No. 40: pp. 14397-14400
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The treatment of readily available N-alkynyl-5-iodo-6-sulfamido-pyrimidines with iPrMgCl center dot LiCl followed by a transmetalation with CuCN center dot 2 LiCl produces, after intramolecular carbocupration, metalated pyrrolo[2,3-d]pyrimidines. Quenching of these pyrimidines with allylic halides or acid chlorides results in polyfunctional pyrrolo[2,3-d]pyrimidines. Further reaction with ICl and a Negishi cross-coupling, using PEPPSI-iPr 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.