Modern approaches to the synthesis of 3-(acylamino)-and 3-(carbamoylamino)benzofuran-2(3 H )-ones (microreview)
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Chemistry of Heterocyclic Compounds 2020, 56(10), 1274–1276
Modern approaches to the synthesis of 3-(acylamino)and 3-(carbamoylamino)benzofuran-2(3H)-ones (microreview) Anatolii I. Sokolov1, Mikhail S. Baranov1,2* 1
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia; е-mail: [email protected] 2 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia; е-mail: [email protected] Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1274–1276
Submitted May 13, 2020 Accepted June 8, 2020
The microreview examines modern approaches to the synthesis of 3-(acylamino)- and 3-(carbamoylamino)benzofuran-2(3H)-ones described over the past 10 years (2011–2020). The methods are subdivided into groups depending on the used starting reagents and the reactions underlying them. Approaches based on the use of phenols as starting compounds, methods of modification of benzofuranone derivatives, as well as some other methods are considered. Introduction The first reporting of derivatives of 3-aminobenzofuranone date back to the middle of the last century.1 However, the interest of the scientific community in such heterocycles increased markedly after the discovery of (–)-fumimycin2 isolated from fungi of the genus Aspergillus fumisynnematus in 2007. The ability to inhibit the bacterial enzyme peptide deformylase, as well as high antibacterial activity
against resistant strains of Staphylococcus aureus make this class of compounds a good basis for the creation of new medicines. In addition, the ability of some 3-aminobenzofuranones to chemiluminescence which occurs in basic media in the presence of O2 is of note. This property can be used to study various redox processes in living systems.3
Reactions of phenols with glyoxylic acid derivatives The reaction of phenols 3 with the products of the condensation of amides,3 ureas,4 and carbamates 1 with glyoxylic acid (2) is traditionally used to synthesize 3-(acylamino)- and 3-(carbamoylamino)benzofuran-2(3H)-ones 4. The reaction requires acid catalysis and is carried out in a one-pot mode, for example, in trifluoroacetic acid. The method covers a wide range of substituents; however, the reaction does not proceed in the presence of acceptor substituents in the starting phenol. Moreover, side reactions occurring during the generation of carbocation sometimes negatively affect product yields. Anatolii Igorevich Sokolov graduated from the Department of Chemistry of the Moscow State University in 2019. He is currently a member of the Group of chemistry of heterocyclic compounds at the Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry. His research interests include chemistry of green fluorescent protein (GFP) chromophore derivatives based on substituted imidazol-5-ones. 0009-3122/20/56(10)-1274©2020 Springer Science+Business Media, LLC
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Mikhail Sergeevich Baranov was born in 1986 in Moscow, Russia. In 2008, he graduated from
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