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功能化-氢化异喹啉-1-酮的简便合成。

A Straightforward Synthesis of Functionalized -Perhydroisoquinolin-1-ones.

机构信息

Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain.

Department of Nutrition, Food Sciences and Gastronomy, Faculty of Pharmacy and Food Sciences, and Institute of Nutrition and Food Safety (INSA-UB), University of Barcelona, 08921 Santa Coloma de Gramanet, Spain.

出版信息

Molecules. 2019 Feb 3;24(3):557. doi: 10.3390/molecules24030557.

DOI:10.3390/molecules24030557
PMID:30717460
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6385050/
Abstract

Base-catalyzed annulation reactions of 5,6-dihydro-2(1)-pyridones with Nazarov-type reagents are reported. The effect of the solvent polarity and the concentration of the reagents is studied. The process involves two successive Michael additions and stereoselectively provides functionalized -perhydroisoquinolin-1-ones.

摘要

本文报道了 5,6-二氢-2(1)-吡啶酮与 Nazarov 型试剂的基底催化环化反应。研究了溶剂极性和试剂浓度的影响。该过程涉及两个连续的迈克尔加成反应,立体选择性地提供了功能化的 -全氢异喹啉-1-酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/c00cc56751c7/molecules-24-00557-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/ca364751d9fd/molecules-24-00557-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/58296d0f3b70/molecules-24-00557-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/5760be792a86/molecules-24-00557-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/58f39312bbdf/molecules-24-00557-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/63466069370e/molecules-24-00557-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/c00cc56751c7/molecules-24-00557-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/ca364751d9fd/molecules-24-00557-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/58296d0f3b70/molecules-24-00557-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/5760be792a86/molecules-24-00557-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/58f39312bbdf/molecules-24-00557-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/63466069370e/molecules-24-00557-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42ed/6385050/c00cc56751c7/molecules-24-00557-sch003.jpg

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本文引用的文献

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Stereocontrolled Annulations of Indolo[2,3-a]quinolizidine-Derived Lactams with a Silylated Nazarov Reagent: Access to Allo and Epiallo Yohimbine-Type Derivatives.手性吲哚[2,3-a]喹啉啶衍生内酰胺与硅烷化 Nazarov 试剂的立体控制环合:获得 allo 和 epiallo 育亨宾型衍生物。
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Pharmacol Res Perspect. 2013 Oct;1(1):e00003. doi: 10.1002/prp2.3. Epub 2013 Sep 17.
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Total syntheses of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via stereoselective C-H insertion and efficient 3,4-stereocontrol.通过立体选择性C-H插入和高效的3,4-立体控制实现(-)-α-红藻氨酸和(+)-α-别红藻氨酸的全合成。
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Pharmacological characterization of the competitive GLUK5 receptor antagonist decahydroisoquinoline LY466195 in vitro and in vivo.竞争性GLUK5受体拮抗剂十氢异喹啉LY466195的体外和体内药理学特性
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