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通过三组分环转化合成硝代芳烃化合物。

Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations.

机构信息

School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.

Center for Equipment and Labour Safety, Vietnam Institute for Building Materials (VIBM), Ministry of Construction, 235 Nguyen Trai, Thanh Xuan, Hanoi 100000, Vietnam.

出版信息

Molecules. 2021 Jan 26;26(3):639. doi: 10.3390/molecules26030639.

DOI:10.3390/molecules26030639
PMID:33530612
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7865560/
Abstract

1-Methyl-3,5-dinitro-2-pyridone serves as an excellent substrate for nucleophilic-type ring transformation because of the electron deficiency and presence of a good leaving group. In this review, we focus on the three-component ring transformation (TCRT) of dinitropyridone involving a ketone and a nitrogen source. When dinitropyridone is allowed to react with a ketone in the presence of ammonia, TCRT proceeds to afford nitropyridines that are not easily produced by alternative procedures. Ammonium acetate can be used as a nitrogen source instead of ammonia to undergo the TCRT, leading to nitroanilines in addition to nitropyridines. In these reactions, dinitropyridone serves as a safe synthetic equivalent of unstable nitromalonaldehyde.

摘要

1-甲基-3,5-二硝基-2-吡啶酮由于其电子缺乏和存在良好的离去基团，是亲核型环转化的理想底物。在本综述中，我们重点介绍了涉及酮和氮源的二硝基吡啶酮的三组分环转化（TCRT）。当二硝基吡啶酮与氨存在下的酮反应时，TCRT 进行，得到不易通过其他方法制备的硝吡啶。醋酸铵可用作氮源代替氨进行 TCRT，除硝吡啶外还可得到硝基苯胺。在这些反应中，二硝基吡啶酮是不稳定的亚硝戊二醛的安全合成等价物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/9122da5450cb/molecules-26-00639-sch013.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/041392e65b07/molecules-26-00639-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/e2b5ef5790ce/molecules-26-00639-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/c772df8a7612/molecules-26-00639-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/f8c764e5c16d/molecules-26-00639-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/a564721cd71e/molecules-26-00639-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/8c84fea58aed/molecules-26-00639-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/49bca5f7c9d8/molecules-26-00639-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/e8b0128d041b/molecules-26-00639-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/4daece199457/molecules-26-00639-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/175a21723343/molecules-26-00639-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/2bc3921aa92b/molecules-26-00639-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/6c36d66d7ba8/molecules-26-00639-sch011.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eaea/7865560/9122da5450cb/molecules-26-00639-sch013.jpg

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