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本文引用的文献

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Intermolecular Dehydrative [4 + 2] Aza-Annulation of N-Arylamides with Alkenes: A Direct and Divergent Entrance to Aza-Heterocycles.N-芳基酰胺与烯烃的分子间脱水[4 + 2]氮杂环化反应:氮杂环化合物的直接且多样化合成途径
Org Lett. 2019 Mar 15;21(6):1681-1685. doi: 10.1021/acs.orglett.9b00233. Epub 2019 Feb 26.
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Amide activation: an emerging tool for chemoselective synthesis.酰胺活化:一种新兴的选择性化学合成工具。
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3
Palladium-catalyzed selective synthesis of 3,4-dihydroquinazolines from electron-rich arylamines, electron-poor arylamines and glyoxalates.钯催化的富电子芳胺、缺电子芳胺和乙二醛选择性合成 3,4-二氢喹唑啉。
Org Biomol Chem. 2018 Jul 11;16(27):5050-5054. doi: 10.1039/c8ob01005f.
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Total synthesis of complex alkaloids by nucleophilic addition to amides.通过酰胺的亲核加成进行复杂生物碱的全合成。
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Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine.通过三氟甲磺酸酐/吡啶促进的酰胺与炔烃反应合成功能化喹啉。
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Synthesis and biological evaluation of fluoro-substituted 3,4-dihydroquinazoline derivatives for cytotoxic and analgesic effects.用于细胞毒性和镇痛作用的氟取代3,4-二氢喹唑啉衍生物的合成及生物学评价
Bioorg Med Chem. 2017 Sep 1;25(17):4656-4664. doi: 10.1016/j.bmc.2017.07.010. Epub 2017 Jul 8.
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3,4-Dihydroquinazoline derivatives inhibit the activities of cholinesterase enzymes.3,4-二氢喹唑啉衍生物可抑制胆碱酯酶的活性。
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Chemoselective reduction of carboxamides.酰胺的选择性还原。
Chem Soc Rev. 2016 Dec 21;45(24):6685-6697. doi: 10.1039/c6cs00244g. Epub 2016 Oct 24.
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Asymmetric Synthesis of Isoquinoline Alkaloids: 2004-2015.异喹啉生物碱的不对称合成:2004-2015 年。
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Synthesis of Highly Functionalized 4-Aminoquinolines.高度官能化 4-氨基喹啉的合成。
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三氟甲磺酸酐促进的 3,4-二氢喹唑啉合成:一种三组分一锅串联反应。

Triflic anhydride mediated synthesis of 3,4-dihydroquinazolines: a three-component one-pot tandem procedure.

机构信息

Department of Chemistry, Lake Superior State University, Sault Sainte Marie, MI 49783, USA.

出版信息

Org Biomol Chem. 2019 Aug 28;17(34):7995-8000. doi: 10.1039/c9ob01596e.

DOI:10.1039/c9ob01596e
PMID:31408069
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6767623/
Abstract

A one-pot three-component tandem reaction involving a key Pictet-Spengler-like annulation step has been developed, providing an efficient method for the synthesis of 3,4-dihydroquinazolines in moderate to good yields from amides, aldehydes, and amines. The multicomponent triflic anhydride mediated reaction tolerates the installation of numerous functional groups, affording extensive diversity about the heterocyclic scaffold.

摘要

发展了一种涉及关键 Pictet-Spengler 型环合步骤的一锅法三组分串联反应,为酰胺、醛和胺合成 3,4-二氢喹唑啉提供了一种从中等到良好收率的有效方法。多组分三氟甲磺酸酐介导的反应能够容忍众多官能团的安装,为杂环支架提供了广泛的多样性。