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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.

DOI:10.3390/molecules22040613
PMID:28406463
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6154686/
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/6154686/6c9a5d92d900/molecules-22-00613-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/a72ad43a0250/molecules-22-00613-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/ea8123b0281e/molecules-22-00613-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/8890454f14e9/molecules-22-00613-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/f9c58418ad14/molecules-22-00613-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/0c56e1ebcd09/molecules-22-00613-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/342b630f5d6a/molecules-22-00613-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/6c9a5d92d900/molecules-22-00613-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/a72ad43a0250/molecules-22-00613-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/ea8123b0281e/molecules-22-00613-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/8890454f14e9/molecules-22-00613-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/f9c58418ad14/molecules-22-00613-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/0c56e1ebcd09/molecules-22-00613-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/342b630f5d6a/molecules-22-00613-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53ac/6154686/6c9a5d92d900/molecules-22-00613-sch004.jpg

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Anal Chim Acta. 2016 May 19;921:84-94. doi: 10.1016/j.aca.2016.03.044. Epub 2016 Apr 7.
2
An efficient lactamisation/N-acyliminium Pictet-Spengler domino strategy for the diasteroselective synthesis of polyhydroxylated quinoxalinone, β-carboline and quinazolinone derivatives.一种用于非对映选择性合成多羟基喹喔啉酮、β-咔啉和喹唑啉酮衍生物的高效内酰胺化/N-酰基亚胺离子 Pictet-Spengler 多米诺策略。
Org Biomol Chem. 2016 May 4;14(18):4276-82. doi: 10.1039/c6ob00250a.
3
Synthetic Entries to and Biological Activity of Pyrrolopyrimidines.
吡咯并嘧啶类的合成方法及生物活性
Chem Rev. 2016 Jan 13;116(1):80-139. doi: 10.1021/acs.chemrev.5b00483. Epub 2015 Dec 23.
4
Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.卤代吡咯并[3,2 - d]嘧啶的抗增殖活性。
Bioorg Med Chem. 2015 Aug 1;23(15):4354-4363. doi: 10.1016/j.bmc.2015.06.025. Epub 2015 Jun 16.
5
Bioactive heterocycles containing endocyclic N-hydroxy groups.含有环内N-羟基的生物活性杂环化合物。
Eur J Med Chem. 2015 Jun 5;97:505-24. doi: 10.1016/j.ejmech.2014.11.031. Epub 2014 Nov 18.
6
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7
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8
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Eur J Pharm Sci. 2014 Aug 1;59:69-82. doi: 10.1016/j.ejps.2014.04.011. Epub 2014 Apr 24.
9
Role of Hydroxamate-Based Histone Deacetylase Inhibitors (Hb-HDACIs) in the Treatment of Solid Malignancies.基于羟肟酸的组蛋白去乙酰化酶抑制剂（Hb-HDACIs）在实体恶性肿瘤治疗中的作用。
Cancers (Basel). 2013 Jul 25;5(3):919-42. doi: 10.3390/cancers5030919.
10
[Bicyclic furano[2,3-D] derivatives of pyrimidine nucleosides--synthesis and antiviral properties].嘧啶核苷的双环呋喃并[2,3 - D]衍生物——合成与抗病毒特性
Bioorg Khim. 2013 Jan-Feb;39(1):26-45. doi: 10.1134/s1068162013010044.