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通过2-乙烯基吲哚或4-呋喃并[3,2-]吲哚与氧代烯丙基阳离子的(4 + 3)环加成反应合成环庚并[]吲哚。

Synthesis of Cyclohepta[]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4-Furo[3,2-]indoles with Oxyallyl Cations.

作者信息

Pirovano Valentina, Brambilla Elisa, Moretti Andrea, Rizzato Silvia, Abbiati Giorgio, Nava Donatella, Rossi Elisabetta

机构信息

Dipartimento di Scienze Farmaceutiche-Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy.

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy.

出版信息

J Org Chem. 2020 Mar 6;85(5):3265-3276. doi: 10.1021/acs.joc.9b03117. Epub 2020 Feb 6.

DOI:10.1021/acs.joc.9b03117
PMID:31975604
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7997566/
Abstract

The synthesis of cyclohepta[]indole derivatives through the dearomative (4 + 3) cycloaddition reaction of 2-vinylindoles or 4-furo[3,2-]indoles with in situ generated oxyallyl cations is reported. Oxyallyl cations are generated from α-bromoketones in the presence of a base and a perfluorinated solvent. Cyclohepta[]indole scaffolds are obtained under mild reaction conditions, in the absence of expensive catalysts, starting from simple reagents, in good to excellent yields and with complete diasteroselectivity. Preliminary expansion of the scope to 3-vinylindoles and to aza-oxyallyl cations is reported.

摘要

报道了通过2-乙烯基吲哚或4-呋喃并[3,2-]吲哚与原位生成的氧代烯丙基阳离子进行去芳构化（4 + 3）环加成反应合成环庚并[]吲哚衍生物。氧代烯丙基阳离子由α-溴代酮在碱和全氟溶剂存在下生成。环庚并[]吲哚骨架在温和的反应条件下，无需昂贵催化剂，从简单试剂出发即可获得，产率良好至优异，且具有完全的非对映选择性。还报道了将该反应范围初步扩展至3-乙烯基吲哚和氮杂氧代烯丙基阳离子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/61fa04712774/jo9b03117_0003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/9e2c1e431b46/jo9b03117_0008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/61fa04712774/jo9b03117_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/adef5adb11e0/jo9b03117_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/87cc3bc6b0bc/jo9b03117_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/c9c3e9fb41ee/jo9b03117_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/d14ebd62566b/jo9b03117_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/585e5678986b/jo9b03117_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/9e2c1e431b46/jo9b03117_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/ed25a4fe457e/jo9b03117_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/c7084df142c6/jo9b03117_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/03927c505937/jo9b03117_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/dc181ceb2819/jo9b03117_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/90c3e4437516/jo9b03117_0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/1bf56b84b546/jo9b03117_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3955/7997566/61fa04712774/jo9b03117_0003.jpg

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2
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3
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Beilstein J Org Chem. 2024 Jun 3;20:1286-1291. doi: 10.3762/bjoc.20.111. eCollection 2024.
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7
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