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在合成面向药理学的化合物过程中，通过碳氢酸对4-氮杂-6-硝基苯并呋咱进行亲核脱芳构化反应。

Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds.

作者信息

Starosotnikov Alexey M, Shkaev Dmitry V, Bastrakov Maxim A, Fedyanin Ivan V, Shevelev Svyatoslav A, Dalinger Igor L

机构信息

N.D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, Moscow 119991, Russia.

A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova str. 28, Moscow 119991, Russia.

出版信息

Beilstein J Org Chem. 2017 Dec 21;13:2854-2861. doi: 10.3762/bjoc.13.277. eCollection 2017.

DOI:10.3762/bjoc.13.277
PMID:29564013
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5753140/
Abstract

4-Aza-6-nitrobenzofuroxan (ANBF) reacts with 1,3-dicarbonyl compounds and other CH acids to give carbon-bonded 1,4-adducts - 1,4-dihydropyridines fused with furoxan ring. In the case of most acidic β-diketones, which exist mainly in the enol form in polar solvents, the reactions proceed in the absence of any added base emphasizing the highly electrophilic character of ANBF. The resulting compounds combine in one molecule NO-donor furoxan ring along with a pharmacologically important 1,4-dihydropyridine fragment and therefore can be considered as prospective platforms for the design of pharmacology-oriented heterocyclic systems.

摘要

4-氮杂-6-硝基苯并呋咱（ANBF）与1,3-二羰基化合物及其他碳氢酸反应，生成与呋咱环稠合的碳键合1,4-加合物——1,4-二氢吡啶。对于大多数酸性β-二酮而言，它们在极性溶剂中主要以烯醇形式存在，反应在未添加任何碱的情况下即可进行，这突出了ANBF的高亲电特性。所生成的化合物在一个分子中结合了一氧化氮供体呋咱环以及具有药理学重要性的1,4-二氢吡啶片段，因此可被视为设计面向药理学的杂环系统的潜在平台。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/796d9c9bb152/Beilstein_J_Org_Chem-13-2854-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/32017cd26b27/Beilstein_J_Org_Chem-13-2854-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/01717ef4cabb/Beilstein_J_Org_Chem-13-2854-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/0643c48590ce/Beilstein_J_Org_Chem-13-2854-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/644c7c238edf/Beilstein_J_Org_Chem-13-2854-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/17a93604dcf2/Beilstein_J_Org_Chem-13-2854-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/db2b77ee1dc3/Beilstein_J_Org_Chem-13-2854-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/dc0477172e1d/Beilstein_J_Org_Chem-13-2854-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/d649aa775c2e/Beilstein_J_Org_Chem-13-2854-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/5571b5e142bc/Beilstein_J_Org_Chem-13-2854-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/796d9c9bb152/Beilstein_J_Org_Chem-13-2854-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/32017cd26b27/Beilstein_J_Org_Chem-13-2854-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/01717ef4cabb/Beilstein_J_Org_Chem-13-2854-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/0643c48590ce/Beilstein_J_Org_Chem-13-2854-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/644c7c238edf/Beilstein_J_Org_Chem-13-2854-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/17a93604dcf2/Beilstein_J_Org_Chem-13-2854-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/db2b77ee1dc3/Beilstein_J_Org_Chem-13-2854-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/dc0477172e1d/Beilstein_J_Org_Chem-13-2854-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/d649aa775c2e/Beilstein_J_Org_Chem-13-2854-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/5571b5e142bc/Beilstein_J_Org_Chem-13-2854-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8a13/5753140/796d9c9bb152/Beilstein_J_Org_Chem-13-2854-g011.jpg

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