Abstract
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.
Dokumententyp: | Zeitschriftenartikel |
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Fakultät: | Chemie und Pharmazie > Department Chemie |
Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
ISSN: | 0947-6539 |
Sprache: | Englisch |
Dokumenten ID: | 48329 |
Datum der Veröffentlichung auf Open Access LMU: | 27. Apr. 2018, 08:15 |
Letzte Änderungen: | 04. Nov. 2020, 13:25 |