The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield the corresponding (S,S)-triflate 2, which is a valuable intermediate in the future synthesis of aminophosphine, to be used in asymmetric catalysis. Preliminarily structural considerations based upon H(1)-NMR spectroscopy are also reported.
{"title":"1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-trifluoromethanesulfonate","authors":"C. Cardellicchio, M. Capozzi","doi":"10.3390/m1695","DOIUrl":"https://doi.org/10.3390/m1695","url":null,"abstract":"The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield the corresponding (S,S)-triflate 2, which is a valuable intermediate in the future synthesis of aminophosphine, to be used in asymmetric catalysis. Preliminarily structural considerations based upon H(1)-NMR spectroscopy are also reported.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41740815","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
28-Acetylbetulin is a good starting compound for the synthesis of 3- or 3,28-substituted betulin derivatives with biological activity. The final product of the reaction of 28-acetylbetulin and acrylic acid under Steglich esterification conditions produced a new 3-alkenyl betulin derivative. The structure of the obtained compound was confirmed based on the analysis of NMR, IR, EI MS, and HRMS spectra. Selected pharmacokinetic parameters related to the absorption and distribution were calculated for the new betulin derivative using in silico methods.
{"title":"28-O-Acetyl-3-O′-(prop-2-enoyl)betulin","authors":"Ewa Bębenek, Elwira Chrobak, Monika Kadela-Tomanek","doi":"10.3390/m1696","DOIUrl":"https://doi.org/10.3390/m1696","url":null,"abstract":"28-Acetylbetulin is a good starting compound for the synthesis of 3- or 3,28-substituted betulin derivatives with biological activity. The final product of the reaction of 28-acetylbetulin and acrylic acid under Steglich esterification conditions produced a new 3-alkenyl betulin derivative. The structure of the obtained compound was confirmed based on the analysis of NMR, IR, EI MS, and HRMS spectra. Selected pharmacokinetic parameters related to the absorption and distribution were calculated for the new betulin derivative using in silico methods.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43566952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Katrina E. Doherty, Arturo León Sandoval, Ethan T. Mercier, N. Leadbeater
The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, green approach. The reaction was performed at room temperature for 3 h, and then the heterocycle was isolated in an analytically pure form by extraction, followed by passing the crude product mixture through a small plug of alumina.
{"title":"3-(4-(Benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine","authors":"Katrina E. Doherty, Arturo León Sandoval, Ethan T. Mercier, N. Leadbeater","doi":"10.3390/m1694","DOIUrl":"https://doi.org/10.3390/m1694","url":null,"abstract":"The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, green approach. The reaction was performed at room temperature for 3 h, and then the heterocycle was isolated in an analytically pure form by extraction, followed by passing the crude product mixture through a small plug of alumina.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46916491","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Perla Islas-Jácome, Cecilia García-Falcón, S. L. Castañón-Alonso, E. Calderon-jaimes, Daniel Canseco-González, A. Islas-Jácome, E. González-Zamora
The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (1H, 13C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS.
{"title":"2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one","authors":"Perla Islas-Jácome, Cecilia García-Falcón, S. L. Castañón-Alonso, E. Calderon-jaimes, Daniel Canseco-González, A. Islas-Jácome, E. González-Zamora","doi":"10.3390/m1693","DOIUrl":"https://doi.org/10.3390/m1693","url":null,"abstract":"The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (1H, 13C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45702793","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (1H, 13C) spectroscopy, Mass (APCI source) spectrometry, elemental analysis, and X-ray crystallography. The title compound may be further functionalized by exploiting the yne moiety, for instance, using click chemistry. The novel pterin derivative, most notably, in contrast to typical pterin behavior, is now soluble or even well soluble in almost any solvent except water.
{"title":"Synthesis, Characterization and Chlorination of 4-(Pentyloxy)-7-(prop-2-yn-1-yloxy)pteridin-2-amine","authors":"Jevy V. Correia, Bruno Wilke, C. Schulzke","doi":"10.3390/m1692","DOIUrl":"https://doi.org/10.3390/m1692","url":null,"abstract":"A new alkyne functionalized pterin derivative was synthesized through a reaction of 7-chloropterin with propargyl alcohol in the presence of sodium hydride. The purity and chemical structure of the compound was validated by NMR (1H, 13C) spectroscopy, Mass (APCI source) spectrometry, elemental analysis, and X-ray crystallography. The title compound may be further functionalized by exploiting the yne moiety, for instance, using click chemistry. The novel pterin derivative, most notably, in contrast to typical pterin behavior, is now soluble or even well soluble in almost any solvent except water.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49444226","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
J. Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, N. Pinaud, Nina Fillová, S. Moreau, Virginie Baylot, V. Desplat
(E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one was designed then synthesized using a multi-step pathway starting from commercially available 2-nitroaniline. Structure characterization of this original substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline shows interesting cytotoxic potential against different human leukemia cell lines (MV4-11, K562, MOLM14 and Jurkat cells).
{"title":"Synthesis, Crystal Structure and Anti-Leukemic Activity of (E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one","authors":"J. Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, N. Pinaud, Nina Fillová, S. Moreau, Virginie Baylot, V. Desplat","doi":"10.3390/m1691","DOIUrl":"https://doi.org/10.3390/m1691","url":null,"abstract":"(E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one was designed then synthesized using a multi-step pathway starting from commercially available 2-nitroaniline. Structure characterization of this original substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline shows interesting cytotoxic potential against different human leukemia cell lines (MV4-11, K562, MOLM14 and Jurkat cells).","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45981505","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A new cobalt(III) complex with a pentadentate Schiff base was synthesized using a reaction of 2,2′-{(2-hydroxypropane-1,3-diyl)bis(nitriloeth-1-yl-1-ylidene)}diphenol (H3L) and cobalt(II) acetate in a methanolic solution. This synthesis resulted in the isolation of dinuclear compound [CoIII2L2] (1), which was characterized using elemental analyses and XRF, FTIR, and TG/DSC techniques. The molecular structure of the complex was confirmed using single-crystal X-ray diffraction. The structure of 1 consists of a centrosymmetric dimer in which two crystallographically equivalent cobalt(III) ions are bridged by two alkoxido oxygen atoms. In addition, each metal center is coordinated by two Schiff bases.
{"title":"Bis(μ2-2,2′-((2-(hydroxy)propane-1,3-diyl)bis((nitrilo)eth-1-yl-1-ylidene))diphenolato)-dicobalt(III)","authors":"A. Bartyzel, B. Cristóvão, D. Osypiuk","doi":"10.3390/m1690","DOIUrl":"https://doi.org/10.3390/m1690","url":null,"abstract":"A new cobalt(III) complex with a pentadentate Schiff base was synthesized using a reaction of 2,2′-{(2-hydroxypropane-1,3-diyl)bis(nitriloeth-1-yl-1-ylidene)}diphenol (H3L) and cobalt(II) acetate in a methanolic solution. This synthesis resulted in the isolation of dinuclear compound [CoIII2L2] (1), which was characterized using elemental analyses and XRF, FTIR, and TG/DSC techniques. The molecular structure of the complex was confirmed using single-crystal X-ray diffraction. The structure of 1 consists of a centrosymmetric dimer in which two crystallographically equivalent cobalt(III) ions are bridged by two alkoxido oxygen atoms. In addition, each metal center is coordinated by two Schiff bases.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48461099","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The preparation and characterization of a new multi-functionalized terpyridine molecule featuring a pyrrole heterocycle and a cyano group is described. This new compound was obtained via a KF/alumina-catalyzed Michael addition of 4′-(pyrrol-2-yl)-2,2′:6′,2″-terpyridine into acrylonitrile. The mild reaction conditions leave the nitrile group unaltered. The title compound was fully characterized via NMR spectroscopy (1H and 13C) as well as via high resolution mass spectrometry and infrared spectroscopy.
{"title":"4′-(N-(2-Cyanoethyl)pyrrol-2-yl)-2,2′:6′,2″-terpyridine","authors":"J. Husson","doi":"10.3390/m1689","DOIUrl":"https://doi.org/10.3390/m1689","url":null,"abstract":"The preparation and characterization of a new multi-functionalized terpyridine molecule featuring a pyrrole heterocycle and a cyano group is described. This new compound was obtained via a KF/alumina-catalyzed Michael addition of 4′-(pyrrol-2-yl)-2,2′:6′,2″-terpyridine into acrylonitrile. The mild reaction conditions leave the nitrile group unaltered. The title compound was fully characterized via NMR spectroscopy (1H and 13C) as well as via high resolution mass spectrometry and infrared spectroscopy.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41792172","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A crystal structure and thermal characterization of a multisite Schiff base containing N2O2-inner and O4-outer coordination sites are reported. The title compound was characterized by X-ray structure analysis, 1H-NMR, 13C-NMR and ATR-FTIR spectroscopy, TG/DSC and TG-FTIR techniques. The compound crystallizes as a methanol solvate in the triclinic system, space group P1¯. The stable at room temperature compound, during heating in the air, first loses a methanol molecule. At higher temperature, the sample decomposition is associated with a strong exothermic effect and the emission of large amounts of carbon dioxide, carbon monoxide and ammonia.
{"title":"N,N′-Bis(3-ethoxy-2-hydroxybenzylidene)-phenylene-1,3-diamine Methanol Solvate","authors":"D. Osypiuk, A. Bartyzel, B. Cristóvão","doi":"10.3390/m1688","DOIUrl":"https://doi.org/10.3390/m1688","url":null,"abstract":"A crystal structure and thermal characterization of a multisite Schiff base containing N2O2-inner and O4-outer coordination sites are reported. The title compound was characterized by X-ray structure analysis, 1H-NMR, 13C-NMR and ATR-FTIR spectroscopy, TG/DSC and TG-FTIR techniques. The compound crystallizes as a methanol solvate in the triclinic system, space group P1¯. The stable at room temperature compound, during heating in the air, first loses a methanol molecule. At higher temperature, the sample decomposition is associated with a strong exothermic effect and the emission of large amounts of carbon dioxide, carbon monoxide and ammonia.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47045710","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
I. Mokrushin, Pavel A. Permyakov, O. A. Pinegina, P. Poturaev, M. Dmitriev, Igor V. Markin
A transparent white crystalline product, K[(C2F5)3PF3] (KFAP), has been synthesized via a one-pot route. Difluorotris(pentafluoroethyl)phosphorane was reacted first with aqueous HF then with K2CO3 or KHCO3 in a solution. Isolation of the intermediate, tris(pentafluoroethyl)trifluorophosphoric acid H[(C2F5)3PF3] (HFAP), was not carried out. The salt has been characterised by powder and single crystal X-ray diffraction. The single-crystal structure shows a monoperiodic coordination polymer involving K∙∙∙F bridging interactions to be present. The thermal characteristics and behaviour of KFAP have been established by simultaneous TGA-DSC measurements.
{"title":"Potassium Trifluorotris(pentafluoroethyl)phosphate","authors":"I. Mokrushin, Pavel A. Permyakov, O. A. Pinegina, P. Poturaev, M. Dmitriev, Igor V. Markin","doi":"10.3390/m1687","DOIUrl":"https://doi.org/10.3390/m1687","url":null,"abstract":"A transparent white crystalline product, K[(C2F5)3PF3] (KFAP), has been synthesized via a one-pot route. Difluorotris(pentafluoroethyl)phosphorane was reacted first with aqueous HF then with K2CO3 or KHCO3 in a solution. Isolation of the intermediate, tris(pentafluoroethyl)trifluorophosphoric acid H[(C2F5)3PF3] (HFAP), was not carried out. The salt has been characterised by powder and single crystal X-ray diffraction. The single-crystal structure shows a monoperiodic coordination polymer involving K∙∙∙F bridging interactions to be present. The thermal characteristics and behaviour of KFAP have been established by simultaneous TGA-DSC measurements.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48593727","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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