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Chemistry of Heterocyclic Compounds最新文献

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Ring-chain isomerism of aldehyde 2-alkylsemicarbazones: experimental and theoretical studies. Novel semicarbazone-based synthesis of 2-alkyl-2,4-dihydro-3H-1,2,4-triazol-3-ones 醛类 2-烷基半咔唑酮的环链异构：实验和理论研究。基于半咔唑酮合成 2-烷基-2,4-二氢-3H-1,2,4-三唑-3-酮的新方法
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-11 DOI: 10.1007/s10593-024-03269-4
{"title":"Ring-chain isomerism of aldehyde 2-alkylsemicarbazones: experimental and theoretical studies. Novel semicarbazone-based synthesis of 2-alkyl-2,4-dihydro-3H-1,2,4-triazol-3-ones","authors":"","doi":"10.1007/s10593-024-03269-4","DOIUrl":"https://doi.org/10.1007/s10593-024-03269-4","url":null,"abstract":"<p> <span> <span> <img alt=\"\" src=\"https://static-content.springer.com/image/MediaObjects/10593_2024_3269_Figa_HTML.png\"/> </span> </span></p> <p>Ring-chain isomerism of aldehyde semicarbazones/1,2,4-triazolidin-3-ones was first studied in detail. Aliphatic aldehyde semicarbazones completely cyclized under the action of very strong Brønsted acids (TfOH, HCl) in aprotic solvents at room temperature to give the corresponding salts of the <em>N</em>1-protonated 1,2,4-triazolidin-3-ones. Both the obtained salts and their free bases are unstable in the presence of air oxygen and undergo slow oxidative aromatization. A novel synthesis of 2-alkyl-2,4-dihydro-3<em>H</em>-1,2,4-triazol-3-ones <em>via</em> the TfOH-promoted cyclization of aliphatic aldehyde semicarbazones followed by aromatization of the isolated crude 1,2,4-triazolidin-3-ones or their hydrotriflates with <em>m</em>-CPBA was developed. In contrast to aliphatic aldehyde semicarbazones, the cyclization of benzaldehyde semicarbazones does not proceed in the presence of strong Brønsted acids. Thermodynamic and kinetic characteristics of the aldehyde semicarbazone ring-chain isomerism are discussed based on the DFT B3LYP/6-311++G(d,p) calculations.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139421514","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}
引用次数: 0
Recent progress in the synthesis of nitroisoxazoles and their hydrogenated analogs via [3+2] cycloaddition reactions (microreview) 通过[3+2]环加成反应合成硝基异噁唑及其氢化类似物的最新进展（微综述）
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03262-x
{"title":"Recent progress in the synthesis of nitroisoxazoles and their hydrogenated analogs via [3+2] cycloaddition reactions (microreview)","authors":"","doi":"10.1007/s10593-024-03262-x","DOIUrl":"https://doi.org/10.1007/s10593-024-03262-x","url":null,"abstract":"<p> <span> <span> <img alt=\"\" src=\"https://static-content.springer.com/image/MediaObjects/10593_2024_3262_Figb_HTML.png\"/> </span> </span></p> <p> <span> <img alt=\"\" src=\"https://static-content.springer.com/image/MediaObjects/10593_2024_3262_Figc_HTML.png\"/> </span> In this microreview, the application of [3+2] cycloaddition reactions for the selective preparation of nitroisoxazoles and their hydrogenated analogs was analyzed on the basis of recent publications. It was found that most discussed processes are realized at room temperature with high or full selectivity.</p> <p><span> <span> <img alt=\"\" src=\"https://static-content.springer.com/image/MediaObjects/10593_2024_3262_Figd_HTML.png\"/> </span> </span></p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408612","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}
引用次数: 0
A [4+2] cycloaddition of push-pull styrenes to 1,2-naphthoquinone 1-methides: a synthesis of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes 推挽式苯乙烯与 1,2-萘醌 1-甲酯的[4+2]环加成反应：2-芳基-2,3-二氢-1H-苯并[f]色烯的合成
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03267-6
Kirill S. Korzhenko, Anastasiya S. Yushkova, Darya A. Rashchepkina, Oleg P. Demidov, Dmitry V. Osipov, Vitaly A. Osyanin
{"title":"A [4+2] cycloaddition of push-pull styrenes to 1,2-naphthoquinone 1-methides: a synthesis of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes","authors":"Kirill S. Korzhenko, Anastasiya S. Yushkova, Darya A. Rashchepkina, Oleg P. Demidov, Dmitry V. Osipov, Vitaly A. Osyanin","doi":"10.1007/s10593-024-03267-6","DOIUrl":"https://doi.org/10.1007/s10593-024-03267-6","url":null,"abstract":"<p>A regioselective and <i>trans</i>-diastereoselective method for the preparation of 2-aryl-2,3-dihydro-1<i>H</i>-benzo[<i>f</i>]chromenes based on 2-naphthol Mannich bases as precursors of 1,2-naphthoquinone 1-methides and highly polarized β-(<i>N</i>,<i>N</i>-dimethylamino)styrene was developed. The resulting cycloadducts were transformed into cyclic acetals and hemiacetals as well as introduced into the Cope reaction leading to 2-aryl-1<i>H</i>-benzo[<i>f</i>]chromenes.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139409400","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}
引用次数: 0
Pseudopeptides based on nicotinic acid with 4-amidoxime unit 基于烟酸和 4-脒肟单元的伪肽
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03270-x
Volodymyr A. Tkachuk, Pavlo V. Reheda, Andriy V. Kozytskiy, Svitlana V. Shishkina, Olga V. Hordiyenko
{"title":"Pseudopeptides based on nicotinic acid with 4-amidoxime unit","authors":"Volodymyr A. Tkachuk, Pavlo V. Reheda, Andriy V. Kozytskiy, Svitlana V. Shishkina, Olga V. Hordiyenko","doi":"10.1007/s10593-024-03270-x","DOIUrl":"https://doi.org/10.1007/s10593-024-03270-x","url":null,"abstract":"<p>The carbodiimide-mediated coupling of 4-cyanonicotinic acid with L-amino acid methyl esters takes place with the predominant formation of bicyclic compounds – methyl 2-(1-imino-3-oxo-1,3-dihydro-2<i>H</i>-pyrrolo[3,4-<i>c</i>]pyridin-2-yl)alkanoates, which are monoimino derivatives of 4-azaphthalimide. Under the action of hydroxylamine they undergo pyrrolidine cycle opening with the formation of pseudopeptides – coupling products of nicotinic acid with amino acid esters bearing an amidoxime function at position 4.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408928","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}
引用次数: 0
Preparation of 2-unsubstituted 5-aryl(hetaryl)-1-hydroxy-1H-imidazoles from of 4-aryl(hetaryl)-1-hydroxy-2,5-dihydro-1H-imidazole-2-carboxylic acid 3-oxides 从 4-芳基（十八烷基）-1-羟基-2,5-二氢-1H-咪唑-2-羧酸 3-氧化物制备 2-未取代的 5-芳基（十八烷基）-1-羟基-1H-咪唑
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03268-5
{"title":"Preparation of 2-unsubstituted 5-aryl(hetaryl)-1-hydroxy-1H-imidazoles from of 4-aryl(hetaryl)-1-hydroxy-2,5-dihydro-1H-imidazole-2-carboxylic acid 3-oxides","authors":"","doi":"10.1007/s10593-024-03268-5","DOIUrl":"https://doi.org/10.1007/s10593-024-03268-5","url":null,"abstract":"<p> <span> <span> <img alt=\"\" src=\"https://static-content.springer.com/image/MediaObjects/10593_2024_3268_Figa_HTML.png\"/> </span> </span></p> <p>Alkylaromatic 1-hydroxyamino-2-oximes reacted at the hydroxyamino group with glyoxylic acid hydrate, providing 4-aryl(hetaryl)-1-hydroxy-2,5-dihydro-1<em>H</em>-imidazole-2-carboxylic acid 3-oxides that were converted upon heating into 5-aryl(hetaryl)-1-hydroxy-1<em>H</em>-imidazoles containing a hydrogen atom at the heterocycle position 2.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408698","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}
引用次数: 0
The synthesis of N-substituted 2-amino-1,4,5,6-tetrahydropyrimidines from isocyanates 从异氰酸酯合成 N-取代的 2-氨基-1,4,5,6-四氢嘧啶
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03280-9
Dmitry S. Ivanov, Alexander Yu. Smirnov, Mikhail S. Baranov
{"title":"The synthesis of N-substituted 2-amino-1,4,5,6-tetrahydropyrimidines from isocyanates","authors":"Dmitry S. Ivanov, Alexander Yu. Smirnov, Mikhail S. Baranov","doi":"10.1007/s10593-024-03280-9","DOIUrl":"https://doi.org/10.1007/s10593-024-03280-9","url":null,"abstract":"<p>A simple procedure for the synthesis of <i>N</i>-substituted 2-amino-1,4,5,6-tetrahydropyrimidines from isocyanates with a wide variety of substituents was developed.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139409339","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}
引用次数: 0
The synthesis of bisquaternary ammonium compounds (microreview) 双季铵化合物的合成（微型综述）
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03266-7
Vyacheslav S. Grinev, Anastasiya A. Lobankova, Alevtina Yu. Yegorova
{"title":"The synthesis of bisquaternary ammonium compounds (microreview)","authors":"Vyacheslav S. Grinev, Anastasiya A. Lobankova, Alevtina Yu. Yegorova","doi":"10.1007/s10593-024-03266-7","DOIUrl":"https://doi.org/10.1007/s10593-024-03266-7","url":null,"abstract":"\u0000<figure></figure><p>Today, the chemistry of quaternary ammonium compounds is rapidly developing field owing, among other things, to the need to combat periodic outbreaks of various infectious diseases, which in some cases assume pandemic proportions. This review summarizes the most recent studies, published mainly over the past 10 years, devoted to advances in the synthesis of bisquaternary ammonium compounds for various purposes. The synthetic methods include monoalkyl halogenation of diamines, dialkyl halogenation of amines, methyltrifluoromethanesulfonation reactions, and anion exchange reactions.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03266-7/MediaObjects/10593_2024_3266_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03266-7/MediaObjects/10593_2024_3266_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408653","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}
引用次数: 0
Methods for the synthesis of 1,3-oxazolidin-2-ones (microreview) 1,3-oxazolidin-2-ones 的合成方法（微综述）
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI: 10.1007/s10593-024-03263-w
Valeria A. Litvinova, Alexander S. Tikhomirov
{"title":"Methods for the synthesis of 1,3-oxazolidin-2-ones (microreview)","authors":"Valeria A. Litvinova, Alexander S. Tikhomirov","doi":"10.1007/s10593-024-03263-w","DOIUrl":"https://doi.org/10.1007/s10593-024-03263-w","url":null,"abstract":"\u0000<figure></figure><p>This microreview is dedicated to new and modified existing methods for the formation of the 1,3-oxazolidin-2-one ring. The material covers key studies published since 2021.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03263-w/MediaObjects/10593_2024_3263_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03263-w/MediaObjects/10593_2024_3263_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408933","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}
引用次数: 0
A new approach to the pyrrolo[3,4-d] pyrimidine system via tandem Staudinger/aza-Wittig reaction of 5-acyl-4-azidomethyl-3,4-dihydropyrimidin-2(1H)-ones 通过 5-酰基-4-叠氮甲基-3,4-二氢嘧啶-2(1H)-酮的串联施陶丁格/扎-维蒂希反应制备吡咯并[3,4-d]嘧啶体系的新方法
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-09 DOI: 10.1007/s10593-024-03273-8
Anastasia A. Fesenko, Mikhail S. Grigoriev, Anatoly D. Shutalev
{"title":"A new approach to the pyrrolo[3,4-d] pyrimidine system via tandem Staudinger/aza-Wittig reaction of 5-acyl-4-azidomethyl-3,4-dihydropyrimidin-2(1H)-ones","authors":"Anastasia A. Fesenko, Mikhail S. Grigoriev, Anatoly D. Shutalev","doi":"10.1007/s10593-024-03273-8","DOIUrl":"https://doi.org/10.1007/s10593-024-03273-8","url":null,"abstract":"<p>A novel access to pyrrolo[3,4-<i>d</i>]pyrimidine scaffold <i>via</i> tandem Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(1-azidoalkyl)-3,4-dihydropyrimidin-2(1<i>H</i>)-ones promoted by PPh<sub>3</sub> was developed. Synthesis of the starting pyrimidinones involved the reaction of readily available <i>N</i>-[(2-azido-1-tosyl)alkyl]ureas with Na enolates of benzoylacetone or acetylacetone followed by acid-catalyzed dehydration of the resulting products without their isolation.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408619","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}
引用次数: 0
Conformationally restricted hydantoins derived from bridgehead functionalized camphorquinones 桥头堡官能化樟脑醌衍生的构象受限海因
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-01-09 DOI: 10.1007/s10593-024-03274-7
Marian V. Gorichko
{"title":"Conformationally restricted hydantoins derived from bridgehead functionalized camphorquinones","authors":"Marian V. Gorichko","doi":"10.1007/s10593-024-03274-7","DOIUrl":"https://doi.org/10.1007/s10593-024-03274-7","url":null,"abstract":"<p>Regio- and stereoselective cleavage of derived camphor α-diketones bearing functional group at the bridgehead position under Bucherer–Bergs reaction conditions was studied for a range of model compounds that are easily accessible from naturally occurring feedstock. In all cases, cleavage of the carbon–carbon bond between the carbonyl groups led to the formation of functionalized hydantoins containing cyclopentane moiety in their structures. Products were obtained in high yields with no purification required, warranting the use of this methodology for the development of libraries of biorelevant compounds.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139408954","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}
引用次数: 0
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