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可见光介导制备用于合成唑吡坦及几种类似物的关键中间体。

Visible Light-Mediated Preparation of a Key Intermediate Employed in the Synthesis of Zolpidem and Several Analogs.

作者信息

Souza Ronei M S, Goulart Tales A C, Pinheiro Roberto do C, Sonaglio Felipe F do C, Simoni Deborah de A, Cormanich Rodrigo A, Jurberg Igor D

机构信息

Department of Organic Chemistry, Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-862, Campinas, SP, Brazil.

Institutional X-Ray Laboratory, Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-862, Campinas, SP, Brazil.

出版信息

Chem Asian J. 2025 Aug;20(16):e00455. doi: 10.1002/asia.202500455. Epub 2025 May 13.

DOI:10.1002/asia.202500455
PMID:40358461
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12392708/
Abstract

This work describes a protocol being only promoted by visible light for the C3-alkylation of imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyridines with aryldiazoacetates. Several known and new analogs of a key intermediate employed in previous syntheses of zolpidem have been accessed in good yields. The preparation of this key intermediate was also achieved using this method, but an adjustment of the nature of the alkylating agent was required.

摘要

这项工作描述了一种仅通过可见光促进咪唑并[1,2 - a]嘧啶和咪唑并[1,2 - a]吡啶与芳基重氮乙酸酯进行C3 - 烷基化反应的方法。在唑吡坦先前合成中使用的关键中间体的几种已知和新的类似物均以良好的产率得到。使用该方法也实现了这种关键中间体的制备,但需要调整烷基化剂的性质。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/9cc15da3e278/ASIA-20-e00455-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/86f593d0e5d0/ASIA-20-e00455-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/9dedaefcf2ff/ASIA-20-e00455-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/2ebc2746183d/ASIA-20-e00455-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/fe9d372d41c7/ASIA-20-e00455-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/9cc15da3e278/ASIA-20-e00455-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/86f593d0e5d0/ASIA-20-e00455-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/9dedaefcf2ff/ASIA-20-e00455-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/2ebc2746183d/ASIA-20-e00455-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/fe9d372d41c7/ASIA-20-e00455-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/84b3/12392708/9cc15da3e278/ASIA-20-e00455-g003.jpg

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本文引用的文献

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Recent Advances in Visible Light-Induced C-H Functionalization of Imidazo[1,2-a]pyridines.咪唑并[1,2 - a]吡啶可见光诱导C - H官能团化的最新进展
Molecules. 2025 Jan 30;30(3):607. doi: 10.3390/molecules30030607.
2
Visible light-mediated formal alkylation and [4+1]-cycloaddition strategies of silyl enol ethers with aryldiazoacetates.可见光介导的硅基烯醇醚与芳基重氮乙酸酯的形式烷基化和[4+1]环加成策略
Chem Commun (Camb). 2025 Jan 28;61(10):2044-2047. doi: 10.1039/d4cc05451b.
3
Synthesis and antimycotic activity of new derivatives of imidazo[1,2-]pyrimidines.
咪唑并[1,2 - ]嘧啶新衍生物的合成及抗真菌活性
Beilstein J Org Chem. 2024 Nov 5;20:2806-2817. doi: 10.3762/bjoc.20.236. eCollection 2024.
4
Imidazopyrimidine: from a relatively exotic scaffold to an evolving structural motif in drug discovery.咪唑并嘧啶:从相对奇特的骨架到药物研发中不断演变的结构基序。
RSC Med Chem. 2024 Mar 13;15(5):1488-1507. doi: 10.1039/d3md00718a. eCollection 2024 May 22.
5
Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.重氮化合物及其前体的可见光诱导反应
Chem Rev. 2024 Jun 12;124(11):7214-7261. doi: 10.1021/acs.chemrev.3c00869. Epub 2024 May 16.
6
Imidazo[1,2-]pyrimidine as a New Antileishmanial Pharmacophore against Promastigotes and Amastigotes.咪唑并[1,2 - ]嘧啶作为一种针对前鞭毛体和无鞭毛体的新型抗利什曼原虫药效基团。
ACS Omega. 2023 Oct 20;8(43):40613-40621. doi: 10.1021/acsomega.3c05441. eCollection 2023 Oct 31.
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Visible light-mediated photolysis of organic molecules: the case study of diazo compounds.可见光照解有机分子:重氮化合物的案例研究。
Chem Commun (Camb). 2023 Jun 13;59(48):7346-7360. doi: 10.1039/d3cc00988b.
8
Recent Developments in the Photochemical Synthesis of Functionalized Imidazopyridines.功能化咪唑并吡啶的光化学合成新进展。
Molecules. 2022 May 27;27(11):3461. doi: 10.3390/molecules27113461.
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Investigation of rotameric conformations of substituted imidazo-[1,2-]pyrazine: experimental and theoretical approaches.取代咪唑并-[1,2-]吡嗪旋转异构体构象的研究:实验与理论方法
RSC Adv. 2018 Mar 7;8(18):9707-9717. doi: 10.1039/c7ra13617j. eCollection 2018 Mar 5.
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