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通过多米诺闭环反应随后进行逆狄尔斯-阿尔德反应合成吡咯并[1,2-a]嘧啶对映体。

Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol.

作者信息

Fekete Beáta, Palkó Márta, Haukka Matti, Fülöp Ferenc

机构信息

Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged H-6720, Hungary.

Department of Chemistry, University of Jyväskylä, FIN-40014 Turku, Finland.

出版信息

Molecules. 2017 Apr 13;22(4):613. doi: 10.3390/molecules22040613.

Abstract

From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products is transferred from norbornene derivatives. The stereochemistry of the synthesized compounds was proven by X-ray crystallography. The absolute configuration of the product is determined by the configuration of the starting amino hydroxamic acid.

摘要

报道了一种从2-氨基降冰片烯异羟肟酸制备吡咯并[1,2-]嘧啶对映体的简单有效方法。该合成基于多米诺环化反应,随后是微波诱导的逆狄尔斯-阿尔德(RDA)反应过程,其中所需产物的手性从降冰片烯衍生物转移而来。合成化合物的立体化学通过X射线晶体学得到证实。产物的绝对构型由起始氨基异羟肟酸的构型决定。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/a72ad43a0250/molecules-22-00613-sch001.jpg

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