通过在完整的二酮哌嗪上构建吡咯环合成吡咯并吡嗪酮。
Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.
作者信息
Maisto Susanna K, Leersnyder Angela P, Pudner Gwyneth L, Scheerer Jonathan R
机构信息
Department of Chemistry, The College of William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.
出版信息
J Org Chem. 2020 Jul 17;85(14):9264-9271. doi: 10.1021/acs.joc.0c01263. Epub 2020 Jun 30.
Abstract
This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicyclic ring fusion. The derived intermediate aldol condensation products, which bear either a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine by protic or gold Lewis acid catalysis.
摘要
本研究揭示了一种合成含有吡咯并二酮哌嗪结构基序的化合物的替代序列。从二酮哌嗪前体开始，温和的羟醛缩合反应先于吡咯环化和双环融合。衍生的中间羟醛缩合产物，带有受保护的羰基或官能化的炔烃，可以通过质子或金路易斯酸催化环化为吡咯并二酮哌嗪。
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