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锰介导的串联三组分多米诺反应：Knoevenagel反应/环化反应/迈克尔加成反应/氧化环化反应合成稠合咪唑并[1,2 -]吡啶类化合物

Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-]pyridines.

作者信息

Storozhenko Olga A, Festa Alexey A, Bella Ndoutoume Delphine R, Aksenov Alexander V, Varlamov Alexey V, Voskressensky Leonid G

机构信息

Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian Federation.

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

出版信息

Beilstein J Org Chem. 2018 Dec 19;14:3078-3087. doi: 10.3762/bjoc.14.287. eCollection 2018.

DOI:10.3762/bjoc.14.287
PMID:30643585
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6317425/
Abstract

The sequential three-component reaction between -hydroxybenzaldehydes, -(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)·2HO or KMnO as stoichiometric oxidants allowed the use of a wide range of nucleophiles, such as nitromethane, (aza)indoles, pyrroles, phenols, pyrazole, indazole and diethyl malonate. The formation of the target compounds presumably proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence.

摘要

已开发出在氧化条件下，α-羟基苯甲醛、α-(氰基甲基)吡啶盐与亲核试剂之间针对取代色烯并咪唑并吡啶的连续三组分反应。使用化学计量的乙酸锰·2H₂O或高锰酸钾作为氧化剂，能够使用多种亲核试剂，如硝基甲烷、(氮杂)吲哚、吡咯、酚类、吡唑、吲唑和丙二酸二乙酯。目标化合物的形成可能是通过多米诺Knoevenagel/环化/迈克尔加成/氧化环化反应序列进行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/da2211821d84/Beilstein_J_Org_Chem-14-3078-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/99a7f5680998/Beilstein_J_Org_Chem-14-3078-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/756bee98d79c/Beilstein_J_Org_Chem-14-3078-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/e45154465a46/Beilstein_J_Org_Chem-14-3078-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/c761d92816fe/Beilstein_J_Org_Chem-14-3078-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/2559e208f21f/Beilstein_J_Org_Chem-14-3078-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/f92d07a1f321/Beilstein_J_Org_Chem-14-3078-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/b15b40494b07/Beilstein_J_Org_Chem-14-3078-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/da2211821d84/Beilstein_J_Org_Chem-14-3078-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/99a7f5680998/Beilstein_J_Org_Chem-14-3078-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/756bee98d79c/Beilstein_J_Org_Chem-14-3078-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/e45154465a46/Beilstein_J_Org_Chem-14-3078-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/c761d92816fe/Beilstein_J_Org_Chem-14-3078-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/2559e208f21f/Beilstein_J_Org_Chem-14-3078-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/f92d07a1f321/Beilstein_J_Org_Chem-14-3078-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/b15b40494b07/Beilstein_J_Org_Chem-14-3078-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/467c/6317425/da2211821d84/Beilstein_J_Org_Chem-14-3078-g009.jpg

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J Org Chem. 2018 Aug 3;83(15):8026-8035. doi: 10.1021/acs.joc.8b00884. Epub 2018 Jun 22.
2
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Org Biomol Chem. 2018 Feb 28;16(9):1402-1418. doi: 10.1039/c7ob02305g.
3
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Org Lett. 2017 Dec 15;19(24):6712-6715. doi: 10.1021/acs.orglett.7b03434. Epub 2017 Dec 5.
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Palladium-Catalyzed Domino Alkenylation/Amination/Pyridination Reactions of 2-Vinylanilines with Alkynes: Access to Cyclopentaquinolines.钯催化的 2-乙烯基苯胺与炔烃的串联烯基化/氨基化/吡啶化反应：环戊并喹啉的合成。
Org Lett. 2017 Dec 15;19(24):6498-6501. doi: 10.1021/acs.orglett.7b03164. Epub 2017 Nov 28.
5
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