175791-65-8Relevant articles and documents
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
Nickel, Johannes,Fernández, Maitane,Klier, Lydia,Knochel, Paul
, p. 14397 - 14400 (2016/09/23)
The treatment of readily available N-alkynyl-5-iodo-6-sulfamido-pyrimidines with iPrMgCl?LiCl followed by a transmetalation with CuCN?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.
TOTAL SYNTHESIS OF A MARINE ALKALOID, RIGIDIN
Sakamoto, Takao,Kondo, Yoshinori,Sato, Shuichiroh,Yamanaka, Hiroshi
, p. 2919 - 2920 (2007/10/02)
Rigidin, a marine alkaloid, was synthesized by the combination of acylation via lithiation and arylation by palladium-catalyzed reaction starting from 2,4-dimethoxypyrrolopyrimidine.