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生成的醛亚胺与琥珀醛之间的一锅法顺序多组分反应：取代吡咯-3-甲醛的简便合成及其在重要药用稠合杂环化合物中的应用。

One-pot sequential multicomponent reaction between generated aldimines and succinaldehyde: facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles.

作者信息

Singh Anoop, Mir Nisar A, Choudhary Sachin, Singh Deepika, Sharma Preetika, Kant Rajni, Kumar Indresh

机构信息

Department of Chemistry, Birla Institute of Technology and Science Pilani 333 031 Rajasthan India

Department of Chemistry Govt. Degree College for Pulwama-192301 J&K India.

出版信息

RSC Adv. 2018 Apr 24;8(28):15448-15458. doi: 10.1039/c8ra01637b. eCollection 2018 Apr 23.

DOI:10.1039/c8ra01637b
PMID:35539447
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9080005/
Abstract

An efficient sequential multi-component method for the synthesis of -arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and generated Ar/HetAr/indolyl-imines, followed by IBX-mediated oxidative aromatization in one-pot operation. The practical utility of this procedure is shown at gram-scale and the synthesis of diverse bioactive fused heterocyclic scaffolds such as pyrroloquinoline, pyrrolo-oxadiazole, dihydro pyrroloquinoline, and pyrrolo-phenanthridine.

摘要

已开发出一种用于合成α-芳基吡咯-3-甲醛的高效顺序多组分方法。该反应涉及脯氨酸催化的丁二醛与生成的Ar/HetAr/吲哚基-亚胺之间的直接曼尼希反应-环化序列，随后通过IBX介导的氧化芳构化进行一锅操作。该方法在克级规模以及多种生物活性稠合杂环支架（如吡咯并喹啉、吡咯并恶二唑、二氢吡咯并喹啉和吡咯并菲啶）的合成中展示了其实用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/0d71f85467ad/c8ra01637b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/ecfb1d139153/c8ra01637b-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/aebfa4dbf582/c8ra01637b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/0ea498dffb03/c8ra01637b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/6f27c4b6627a/c8ra01637b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/0d71f85467ad/c8ra01637b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/ecfb1d139153/c8ra01637b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/fe4e5daaaf3c/c8ra01637b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/44170cf7ed4d/c8ra01637b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/aebfa4dbf582/c8ra01637b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/0ea498dffb03/c8ra01637b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/6f27c4b6627a/c8ra01637b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/10bb/9080005/0d71f85467ad/c8ra01637b-s5.jpg

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本文引用的文献

1
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Chem Sci. 2015 Nov 1;6(11):6448-6455. doi: 10.1039/c5sc02322j. Epub 2015 Aug 3.
2
A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis.通过过渡金属催化合成β-取代吡咯的通用方法。
J Org Chem. 2016 Feb 19;81(4):1450-60. doi: 10.1021/acs.joc.5b02581. Epub 2016 Feb 4.
3
Acid-Promoted Cross-Dehydrative Aromatization for the Synthesis of Tetraaryl-Substituted Pyrroles.
碘(V)基氧化剂在氧化反应中的应用。
Molecules. 2023 Jul 6;28(13):5250. doi: 10.3390/molecules28135250.
4
Recent approaches in the organocatalytic synthesis of pyrroles.吡咯有机催化合成的最新方法。
RSC Adv. 2021 Apr 13;11(22):13585-13601. doi: 10.1039/d1ra01690c. eCollection 2021 Apr 7.
5
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Front Chem. 2022 Feb 28;10:841751. doi: 10.3389/fchem.2022.841751. eCollection 2022.
6
Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access -(hetero)aryl-4,5-unsubstituted pyrroles.芳香胺、1,3 - 二羰基化合物与α - 溴乙醛缩二乙醇的三组分反应，用于合成-(杂)芳基 - 4,5 - 未取代的吡咯。
Beilstein J Org Chem. 2020 Nov 30;16:2920-2928. doi: 10.3762/bjoc.16.241. eCollection 2020.
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6
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7
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8
A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles.铜催化的卤代乙烯基和carbazates 的偶联反应：在多取代吡咯的组装中的应用。
Chem Commun (Camb). 2014 Mar 21;50(23):3085-8. doi: 10.1039/c3cc49724k.
9
Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant.使用 Pd(OAc)2 催化的烯酰胺和炔烃与分子氧作为氧化剂合成多取代吡咯。
Chem Commun (Camb). 2014 Mar 14;50(21):2784-6. doi: 10.1039/c3cc49683j.
10
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Chem Sci. 2014 Jan 1;5(1):151-155. doi: 10.1039/C3SC52572D.