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通过一锅法三组分反应高效合成新型稠合 5H-呋喃并[2,3-d]噻唑并[3,2-a]嘧啶-5-酮。

An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction.

机构信息

Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran.

Department of Chemistry, Tulane University, New Orleans, LA, USA.

出版信息

Mol Divers. 2022 Feb;26(1):183-190. doi: 10.1007/s11030-020-10173-4. Epub 2021 Jan 3.

DOI:10.1007/s11030-020-10173-4
PMID:33389558
Abstract

Herein, a convenient and efficient synthesis of 7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives was achieved from the reaction of isoquinolinium N-ylides, aromatic aldehydes, and heterocyclic 1,3-dicarbonyl compounds via one-pot three-component diastereoselective domino reaction in good-to-excellent yields. The advantages of this protocol are easily available starting materials, operational simplicity, and avoidance of hazardous organic solvents and catalyst. The synthesized products were characterized by IR, H NMR, C NMR and mass spectra. Additionally, the conclusive structure of target compounds was confirmed by X-Ray diffraction analysis.

摘要

本文实现了一种简便高效的合成 7-苯甲酰基-6-(芳基)-6,7-二氢-5H-呋喃并[2,3-d]噻唑并[3,2-a]嘧啶-5-酮衍生物的方法,该方法是通过一锅法三组分非对映选择性稠合反应,由异喹啉𬭩 N-叶立德、芳香醛和杂环 1,3-二羰基化合物反应得到,产率良好至优秀。该方法的优点是起始原料易得、操作简单、避免了使用危险的有机溶剂和催化剂。所合成的产物通过 IR、H NMR、C NMR 和质谱进行了表征。此外,通过 X 射线衍射分析确认了目标化合物的确定结构。

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1
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Org Biomol Chem. 2019 Apr 17;17(16):3978-3983. doi: 10.1039/c9ob00166b.
2
Stepwise cycloaddition reaction of N-phenacylbenzothiazolium bromides and nitroalkenes for tetrahydro-, dihydro- and benzo[d]pyrrolo[2,1-b]thiazoles.N-苯甲酰基苯并噻唑溴化物与硝基烯烃用于合成四氢、二氢和苯并[d]吡咯并[2,1-b]噻唑的逐步环加成反应。
Sci Rep. 2017 Apr 13;7:46470. doi: 10.1038/srep46470.
3
Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile.
通过异喹啉盐、靛红和丙二腈的三组分反应形成多样的多环螺环氧化吲哚。
Sci Rep. 2017 Jan 20;7:41024. doi: 10.1038/srep41024.
4
Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles.通过N-苯甲酰基苯并噻唑溴化物与3-亚甲基氧化吲哚的环加成反应实现螺[苯并[d]吡咯并[2,1-b]噻唑-3,3'-吲哚啉]的非对映选择性合成。
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J Org Chem. 2013 Jun 7;78(11):5505-20. doi: 10.1021/jo400621r. Epub 2013 May 22.
8
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J Org Chem. 2012 Jan 20;77(2):1191-7. doi: 10.1021/jo2023312. Epub 2012 Jan 3.
9
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Bioorg Med Chem. 2009 Oct 15;17(20):7324-36. doi: 10.1016/j.bmc.2009.08.044. Epub 2009 Aug 22.
10
Rational design of 4-amino-5,6-diaryl-furo[2,3-d]pyrimidines as potent glycogen synthase kinase-3 inhibitors.4-氨基-5,6-二芳基-呋喃并[2,3-d]嘧啶作为强效糖原合酶激酶-3抑制剂的合理设计
Bioorg Med Chem Lett. 2008 Mar 15;18(6):1967-71. doi: 10.1016/j.bmcl.2008.01.113. Epub 2008 Feb 2.