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一种不寻常的亚硫酰氯促进的碳-碳键形成反应以制备4,4'-联吡唑啉酮。

An unusual thionyl chloride-promoted C-C bond formation to obtain 4,4'-bipyrazolones.

作者信息

Eller Gernot A, Vilkauskaitė Gytė, Šačkus Algirdas, Martynaitis Vytas, Mamuye Ashenafi Damtew, Pace Vittorio, Holzer Wolfgang

机构信息

Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria.

Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania.

出版信息

Beilstein J Org Chem. 2018 Jun 4;14:1287-1292. doi: 10.3762/bjoc.14.110. eCollection 2018.

DOI:10.3762/bjoc.14.110
PMID:29977396
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6009192/
Abstract

Dialkyl 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates are readily obtained by the reaction of 5-hydroxypyrazole-4-carboxylates in refluxing thionyl chloride. The obtained diesters can be transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent decarboxylation. Detailed NMR spectroscopic investigations (H, C, N) were undertaken with all products prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis.

摘要

5-羟基吡唑-4-羧酸酯在回流的亚硫酰氯中反应可轻松制得二烷基5,5'-二氧代-4,4'-联吡唑-4,4'-二羧酸酯。所得二酯可通过碱性水解及随后的脱羧反应转化为相应的4,4'-联吡唑。对制备的所有产物进行了详细的核磁共振光谱研究（氢、碳、氮）。此外，通过X射线晶体结构分析确定了一种代表性的5,5'-二氧代-4,4'-联吡唑-4,4'-二羧酸酯的结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/b80ceddb2877/Beilstein_J_Org_Chem-14-1287-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/ddf5a3df9dfe/Beilstein_J_Org_Chem-14-1287-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/77befc10a2a8/Beilstein_J_Org_Chem-14-1287-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/cfdf7367d81d/Beilstein_J_Org_Chem-14-1287-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/e00637d7fa7a/Beilstein_J_Org_Chem-14-1287-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/2696268a2254/Beilstein_J_Org_Chem-14-1287-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/30663471069c/Beilstein_J_Org_Chem-14-1287-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/a9eb43b3a2b7/Beilstein_J_Org_Chem-14-1287-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/19aadde0a0d3/Beilstein_J_Org_Chem-14-1287-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/42f4dcc29647/Beilstein_J_Org_Chem-14-1287-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/62db22a2904d/Beilstein_J_Org_Chem-14-1287-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/b80ceddb2877/Beilstein_J_Org_Chem-14-1287-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/ddf5a3df9dfe/Beilstein_J_Org_Chem-14-1287-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/77befc10a2a8/Beilstein_J_Org_Chem-14-1287-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/cfdf7367d81d/Beilstein_J_Org_Chem-14-1287-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/e00637d7fa7a/Beilstein_J_Org_Chem-14-1287-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/2696268a2254/Beilstein_J_Org_Chem-14-1287-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/30663471069c/Beilstein_J_Org_Chem-14-1287-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/a9eb43b3a2b7/Beilstein_J_Org_Chem-14-1287-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/19aadde0a0d3/Beilstein_J_Org_Chem-14-1287-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/42f4dcc29647/Beilstein_J_Org_Chem-14-1287-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/62db22a2904d/Beilstein_J_Org_Chem-14-1287-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b216/6009192/b80ceddb2877/Beilstein_J_Org_Chem-14-1287-g005.jpg

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