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用于高效合成1,3,4-恶二唑的硝基烷烃的亲电活化

Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles.

作者信息

Aksenov Alexander V, Khamraev Vladislav, Aksenov Nicolai A, Kirilov Nikita K, Domenyuk Dmitriy A, Zelensky Vladimir A, Rubin Michael

机构信息

Department of Chemistry, North Caucasus Federal University 1a Pushkin St. Stavropol 355009 Russian Federation

Department of General Practice Dentistry and Child Dentistry, Stavropol State Medical University 310 Mira Street Stavropol 355017 Russian Federation.

出版信息

RSC Adv. 2019 Feb 26;9(12):6636-6642. doi: 10.1039/c9ra00976k. eCollection 2019 Feb 22.

DOI:10.1039/c9ra00976k
PMID:35518500
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9060929/
Abstract

A novel methodology for general and chemoselective preparation of non-symmetric 1,3,4-oxadiazoles is developed. This unusual reaction proceeds polyphosphoric acid-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides.

摘要

开发了一种用于一般和化学选择性制备非对称1,3,4-恶二唑的新方法。这种不同寻常的反应是在多磷酸辅助下,使硝基烷烃对酰肼进行亲核攻击而进行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/f9e91e2c8eaa/c9ra00976k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/bdb89fc9616d/c9ra00976k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/74905757497c/c9ra00976k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/ea1effd659fe/c9ra00976k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/79bb6bc24ac1/c9ra00976k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/f9e91e2c8eaa/c9ra00976k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/bdb89fc9616d/c9ra00976k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/74905757497c/c9ra00976k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/ea1effd659fe/c9ra00976k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/79bb6bc24ac1/c9ra00976k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bca3/9060929/f9e91e2c8eaa/c9ra00976k-f2.jpg

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Org Lett. 2015 Jun 19;17(12):2960-3. doi: 10.1021/acs.orglett.5b01241. Epub 2015 Jun 2.
2
Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes.通过苯胺与硝基烷烃的亲核加成反应制备苯并咪唑和苯并恶唑。
Org Biomol Chem. 2015 Apr 14;13(14):4289-95. doi: 10.1039/c5ob00131e. Epub 2015 Mar 11.
3
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4
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5
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6
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4
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7
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8
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9
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10
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