Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.020
Ivan V. Smirnov , Oleg I. Afanasyev , Klim O. Biriukov , Maria I. Godovikova , Denis A. Chusov
Arene manganese π-complex was applied as a catalyst for the reductive Knoevenagel condensation. Syngas was used as a selective synergistic reducing agent providing the possibility to use 3d metal-based catalyst in such process. Demonstrated substrate scope indicates a high potential for this reaction in a medicinal chemistry.
{"title":"Mn-catalyzed syngas-assisted reductive Knoevenagel condensation","authors":"Ivan V. Smirnov , Oleg I. Afanasyev , Klim O. Biriukov , Maria I. Godovikova , Denis A. Chusov","doi":"10.1016/j.mencom.2024.10.020","DOIUrl":"10.1016/j.mencom.2024.10.020","url":null,"abstract":"<div><div>Arene manganese π-complex was applied as a catalyst for the reductive Knoevenagel condensation. Syngas was used as a selective synergistic reducing agent providing the possibility to use 3d metal-based catalyst in such process. Demonstrated substrate scope indicates a high potential for this reaction in a medicinal chemistry.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 831-833"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.032
Vladimir V. Baranov , Maria M. Antonova , Svetlana A. Aksenova , Natalya G. Kolotyrkina , Angelina N. Kravchenko
New regioselective reaction of 1-alkyl-5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-one with alkylureas gives predominantly 1,6-dialkyl-3a,6a-diphenylglycolurils along with minor quantities of the 1,4-isomers. In case of propyl homologues, co-crystal of 1,6/1,4-dipropyl glycolurils would precipitate. Based on the analysis of the crystal packing of the products, new type of supramolecular chains for 1,4-disubstituted glycolurils has been identified.
{"title":"Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization","authors":"Vladimir V. Baranov , Maria M. Antonova , Svetlana A. Aksenova , Natalya G. Kolotyrkina , Angelina N. Kravchenko","doi":"10.1016/j.mencom.2024.10.032","DOIUrl":"10.1016/j.mencom.2024.10.032","url":null,"abstract":"<div><div>New regioselective reaction of 1-alkyl-5-hydroxy-4,5-diphenyl-1<em>H</em>-imidazol-2(5<em>H</em>)-one with alkylureas gives predominantly 1,6-dialkyl-3a,6a-diphenylglycolurils along with minor quantities of the 1,4-isomers. In case of propyl homologues, co-crystal of 1,6/1,4-dipropyl glycolurils would precipitate. Based on the analysis of the crystal packing of the products, new type of supramolecular chains for 1,4-disubstituted glycolurils has been identified.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 871-874"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743923","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.033
Konstantin E. Shepelenko , Irina G. Gnatiuk , Andrey A. Aleksandrov , Mikhail E. Minyaev , Victor M. Chernyshev
The ruthenium-catalyzed reaction of 2-(het)aryl-1-methyl- perimidines with aryl bromides proceeds as regioselective CH ortho-arylation of the (het)aryl fragment, perimidine core acting as a directing group. The reaction is selective and tolerates to different functional groups in aryl bromide thus allowing further functionalization of the obtained products.
{"title":"Regioselective arylation of (het)aryl fragment in 2-(het)aryl-1-methylperimidines under ruthenium catalysis","authors":"Konstantin E. Shepelenko , Irina G. Gnatiuk , Andrey A. Aleksandrov , Mikhail E. Minyaev , Victor M. Chernyshev","doi":"10.1016/j.mencom.2024.10.033","DOIUrl":"10.1016/j.mencom.2024.10.033","url":null,"abstract":"<div><div>The ruthenium-catalyzed reaction of 2-(het)aryl-1-methyl- perimidines with aryl bromides proceeds as regioselective C<img>H <em>ortho</em>-arylation of the (het)aryl fragment, perimidine core acting as a directing group. The reaction is selective and tolerates to different functional groups in aryl bromide thus allowing further functionalization of the obtained products.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 875-877"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743924","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.019
Kirill V. Agliulin , Andrey V. Stepanov , Vladimir N. Yarovenko , Mikhail M. Krayushkin , Evgeny V. Tretyakov , Darina I. Nasyrova , Valentina V. Ilyushenkova , Anton O. Ayt , Tatyana M. Valova
A new hybrid chromone derivative bearing α-bromofuryl, p-(iminomethyl)benzoyl and 2,2,6,6-tetramethylpiperidin-1- oxyl moieties was synthesized by the azomethine reaction involving 4-amino-TEMPO. The benzoyl moiety in this paramagnetic molecule is almost perpendicular to the chromone plane. Having been exposed to UV light, this paramagnet undergoes a transformation accompanied by appearance of intense absorption and luminescence bands with maxima at 420 and 500 nm, respectively, i.e., the presence of paramagnetic moiety does not interfere with generation of fluorescence.
{"title":"Synthesis, structure and properties of spin-labeled photosensitive chromone derivative","authors":"Kirill V. Agliulin , Andrey V. Stepanov , Vladimir N. Yarovenko , Mikhail M. Krayushkin , Evgeny V. Tretyakov , Darina I. Nasyrova , Valentina V. Ilyushenkova , Anton O. Ayt , Tatyana M. Valova","doi":"10.1016/j.mencom.2024.10.019","DOIUrl":"10.1016/j.mencom.2024.10.019","url":null,"abstract":"<div><div>A new hybrid chromone derivative bearing α-bromofuryl, <em>p</em>-(iminomethyl)benzoyl and 2,2,6,6-tetramethylpiperidin-1- oxyl moieties was synthesized by the azomethine reaction involving 4-amino-TEMPO. The benzoyl moiety in this paramagnetic molecule is almost perpendicular to the chromone plane. Having been exposed to UV light, this paramagnet undergoes a transformation accompanied by appearance of intense absorption and luminescence bands with maxima at 420 and 500 nm, respectively, <em>i.e</em>., the presence of paramagnetic moiety does not interfere with generation of fluorescence.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 828-830"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743828","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.008
Sergey V. Trepalin , Pavel V. Komarov , Andrey A. Knizhnik , Denis B. Shirabaykin , Alexander S. Sinitsa , Boris V. Potapkin
A method for assessing the synthesis complexity of in silico designed polymers using the modified Synthetic Accessibility Score Index is presented. This index is calculated by decomposing a chemical structure into smaller fragments and evaluating their contribution to the overall score. Also discussed are the data sources for these estimates, ways to overcome ambiguity in the representation of the smallest repeating unit of polymers, and the problem of evaluating the stability of chemical structures stored in machine- generated databases.
{"title":"On evaluating the possibility of synthesizing virtually designed polymers","authors":"Sergey V. Trepalin , Pavel V. Komarov , Andrey A. Knizhnik , Denis B. Shirabaykin , Alexander S. Sinitsa , Boris V. Potapkin","doi":"10.1016/j.mencom.2024.10.008","DOIUrl":"10.1016/j.mencom.2024.10.008","url":null,"abstract":"<div><div>A method for assessing the synthesis complexity of <em>in silico</em> designed polymers using the modified Synthetic Accessibility Score Index is presented. This index is calculated by decomposing a chemical structure into smaller fragments and evaluating their contribution to the overall score. Also discussed are the data sources for these estimates, ways to overcome ambiguity in the representation of the smallest repeating unit of polymers, and the problem of evaluating the stability of chemical structures stored in machine- generated databases.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 792-794"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743809","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.014
Yan V. Demyanov , Irina Yu. Bagryanskaya , Alexander V. Artem’ev
The interaction of tris(6-methyl-2-pyridyl)phosphine oxide (L) with equimolar amounts of [Cu(MeCN)4]PF6 or AgClO4 in acetonitrile produces scorpionate-like complexes [M(L)(MeCN)]X (M = Cu and Ag; X = and ). At ambient temperature, these compounds exhibit orange (λmax = 608 nm) or turquoise (λmax = 490 nm) photo-luminescence with a quantum yield up to 16% and lifetimes of microsecond order.
{"title":"CuI and AgI scorpionate-like complexes based on sterically hindered tris(6-methyl-2-pyridyl)phosphine oxide","authors":"Yan V. Demyanov , Irina Yu. Bagryanskaya , Alexander V. Artem’ev","doi":"10.1016/j.mencom.2024.10.014","DOIUrl":"10.1016/j.mencom.2024.10.014","url":null,"abstract":"<div><div>The interaction of tris(6-methyl-2-pyridyl)phosphine oxide (L) with equimolar amounts of [Cu(MeCN)<sub>4</sub>]PF<sub>6</sub> or AgClO<sub>4</sub> in acetonitrile produces scorpionate-like complexes [M(L)(MeCN)]X (M = Cu and Ag; X = <span><math><msubsup><mi>PF</mi><mn>6</mn><mo>-</mo></msubsup></math></span> and <span><math><msubsup><mi>ClO</mi><mn>4</mn><mo>-</mo></msubsup></math></span>). At ambient temperature, these compounds exhibit orange (<em>λ</em><sub>max</sub> = 608 nm) or turquoise (<em>λ</em><sub>max</sub> = 490 nm) photo-luminescence with a quantum yield up to 16% and lifetimes of microsecond order.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 812-814"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743815","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.017
Oleg V. Khazipov, Anastasia S. Pyatachenko, Victor M. Chernyshev
A user-friendly and highly efficient mechanochemical synthesis of Ni/NHC complexes of the general formula (NHC)Ni(Cp)Cl (NHC is an N-heterocyclic carbene ligand; Cp is the cyclopentadienyl anion) under aerobic conditions is reported. The reaction between nickelocene and azolium salts (NHC proligands) proceeds with good to excellent yields of (NHC)Ni(Cp)Cl in the presence of a K2CO3 additive, which reduces the clumping of the reaction mixture. The developed process can be scaled up on a planetary ball mill.
{"title":"A novel mechanochemical synthesis of cyclopentadienyl-type Ni/NHC complexes","authors":"Oleg V. Khazipov, Anastasia S. Pyatachenko, Victor M. Chernyshev","doi":"10.1016/j.mencom.2024.10.017","DOIUrl":"10.1016/j.mencom.2024.10.017","url":null,"abstract":"<div><div>A user-friendly and highly efficient mechanochemical synthesis of Ni/NHC complexes of the general formula (NHC)Ni(Cp)Cl (NHC is an N-heterocyclic carbene ligand; Cp is the cyclopentadienyl anion) under aerobic conditions is reported. The reaction between nickelocene and azolium salts (NHC proligands) proceeds with good to excellent yields of (NHC)Ni(Cp)Cl in the presence of a K<sub>2</sub>CO<sub>3</sub> additive, which reduces the clumping of the reaction mixture. The developed process can be scaled up on a planetary ball mill.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 822-824"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743826","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.026
Marina A. Katkova , Galina S. Zabrodina , Roman V. Rumyantcev , Grigory Yu. Zhigulin , Ivan V. Skabitsky , Irina G. Fomina , Olga B. Bekker , Sergey Yu. Ketkov , Igor L. Eremenko
A new 3-hydroxy-4-pyridinone ligand, viz. N-(3-hydroxy-2-methyl-4-oxo-4H-pyridin-1-yl)isonicotinamide bearing isoniazid fragment, was synthesized and characterized. The differences in molecular and electronic structures of the product compared to the parent isoniazid (INH) were revealed by X-ray diffraction and DFT calculations. They are responsible for a dramatic decrease in the antimyco- bacterial activity of the product in comparison with INH.
{"title":"Insight into design of 3-hydroxy-4-pyridinone functionalized with isoniazid fragment: structural characterization and antimycobacterial evaluation","authors":"Marina A. Katkova , Galina S. Zabrodina , Roman V. Rumyantcev , Grigory Yu. Zhigulin , Ivan V. Skabitsky , Irina G. Fomina , Olga B. Bekker , Sergey Yu. Ketkov , Igor L. Eremenko","doi":"10.1016/j.mencom.2024.10.026","DOIUrl":"10.1016/j.mencom.2024.10.026","url":null,"abstract":"<div><div>A new 3-hydroxy-4-pyridinone ligand, <em>viz</em>. <em>N</em>-(3-hydroxy-2-methyl-4-oxo-4<em>H</em>-pyridin-1-yl)isonicotinamide bearing isoniazid fragment, was synthesized and characterized. The differences in molecular and electronic structures of the product compared to the parent isoniazid (INH) were revealed by X-ray diffraction and DFT calculations. They are responsible for a dramatic decrease in the antimyco- bacterial activity of the product in comparison with INH.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 850-853"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743917","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.030
Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Artem N. Fakhrutdinov, Mikhail P. Egorov
The new type of four-component tandem Knoevenagel–Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings.
{"title":"First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings","authors":"Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Artem N. Fakhrutdinov, Mikhail P. Egorov","doi":"10.1016/j.mencom.2024.10.030","DOIUrl":"10.1016/j.mencom.2024.10.030","url":null,"abstract":"<div><div>The new type of four-component tandem Knoevenagel–Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as <sup>1</sup>H-<sup>1</sup>H COSY, <sup>1</sup>H-<sup>13</sup>C HSQC, and <sup>1</sup>H-<sup>13</sup>C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 865-867"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743921","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-01DOI: 10.1016/j.mencom.2024.10.041
Anton E. Dzhusupov , Evgeniy O. Pentsak
Formation of metallic nickel nanoparticles was observed during nickel catalyst activation in hydrogen flow at high temperature. The scale of change in catalyst morphology was determined via identical location electron microscopy.
研究了高温氢流活化镍催化剂过程中金属镍纳米颗粒的形成。通过同位电镜测定催化剂形态变化的尺度。
{"title":"Nickel nanoparticles formation during Ni catalyst activation revealed by identical location electron microscopy","authors":"Anton E. Dzhusupov , Evgeniy O. Pentsak","doi":"10.1016/j.mencom.2024.10.041","DOIUrl":"10.1016/j.mencom.2024.10.041","url":null,"abstract":"<div><div>Formation of metallic nickel nanoparticles was observed during nickel catalyst activation in hydrogen flow at high temperature. The scale of change in catalyst morphology was determined <em>via</em> identical location electron microscopy.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 6","pages":"Pages 899-901"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743931","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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