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通过氟化腈亚胺与查尔酮的顺序（3 + 2）环加成反应和溶剂依赖性脱酰氧化反应制备三氟甲基化吡唑。

Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions.

作者信息

Kowalczyk Anna, Utecht-Jarzyńska Greta, Mlostoń Grzegorz, Jasiński Marcin

机构信息

Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91403 Łódź, Poland.

The University of Lodz Doctoral School of Exact and Natural Sciences, Banacha 12/16, 90237 Łódź, Poland.

出版信息

Org Lett. 2022 Apr 8;24(13):2499-2503. doi: 10.1021/acs.orglett.2c00521. Epub 2022 Mar 28.

DOI:10.1021/acs.orglett.2c00521
PMID:35343703
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9003577/
Abstract

A general approach for preparation of two types of polyfunctionalized 3-trifluoromethylpyrazoles is reported. The protocol comprises (3 + 2)-cycloaddition of the generated trifluoroacetonitrile imines with enones leading to -configured 5-acyl-pyrazolines in a fully regio- and diastereoselective manner. Initially formed cycloadducts were aromatized by treatment with manganese dioxide. Depending on the solvent used, the oxidation step either led to fully substituted pyrazoles (DMSO) or proceeded via a deacylative pathway to afford 1,3,4-trisubstituted derivatives (hexane) with excellent selectivity.

摘要

报道了一种制备两种类型多官能化3-三氟甲基吡唑的通用方法。该方案包括生成的三氟乙腈亚胺与烯酮的(3 + 2)环加成反应，以完全区域和非对映选择性的方式生成构型为-的5-酰基吡唑啉。最初形成的环加成物通过用二氧化锰处理进行芳构化。根据所用溶剂的不同，氧化步骤要么导致完全取代的吡唑（二甲基亚砜），要么通过脱酰途径得到具有优异选择性的1,3,4-三取代衍生物（己烷）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/3bbecc3dbab6/ol2c00521_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/ab06f0a9d073/ol2c00521_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/7b71c5c37cac/ol2c00521_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/d26c877e2f6e/ol2c00521_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/3bbecc3dbab6/ol2c00521_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/ab06f0a9d073/ol2c00521_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/7b71c5c37cac/ol2c00521_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/d26c877e2f6e/ol2c00521_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/12be/9003577/3bbecc3dbab6/ol2c00521_0004.jpg

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