Journal of Heterocyclic Chemistry最新文献

{"title":"Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents","authors":"Altaf S. Almatari,&nbsp;Ali Saeed,&nbsp;Ghada E. Abdel-Ghani,&nbsp;Mahmood M. S. Abdullah,&nbsp;Amr El-Demerdash,&nbsp;Ehab Abdel-Latif","doi":"10.1002/jhet.4832","DOIUrl":"10.1002/jhet.4832","url":null,"abstract":"<p>The objective of this study is to synthesize novel heterocyclic scaffolds containing a thiophene moiety using easily accessible acetoacetamide as a key synthon. The reaction of acetoacetamide with diazonium salts resulted in the formation of the corresponding thiophene derivatives <b>4a</b>–<b>c</b>. Additionally, the reaction of acetoacetamide derivative <b>3</b> with malononitrile, ethyl cyanoacetate, or 2-cyanoacetamide, along with elemental sulfur, under refluxing in dioxane containing triethylamine afforded thiophene-containing derivatives <b>5a</b>–<b>c</b>. Furthermore, compound <b>3</b> reacted with phenyl isothiocyanate in dry dimethylformamide and K₂CO₃ to yield compound <b>7</b>. In situ alkylation of the non-isolable salt <b>6</b> was achieved by the addition of methyl iodide, resulting in the formation of methylthio-thiophene-2-carboxamide <b>8</b>. Compound <b>7</b> was employed with numerous alpha-halogenated reagents in ethanol, affording thiazole derivative <b>9</b> and thiophene derivatives <b>10a</b> and <b>10b</b>, respectively. Moreover, compound <b>8</b> was reacted with hydrazine to produce the 1<i>H</i>-pyrazole-4-carboxamide derivative <b>11</b>. Additionally, refluxing acetoacetamide derivative <b>3</b> with malononitrile and/or ethyl cyanoacetate in dioxane, in the presence of catalytic amount of triethylamine afforded 4-imino-3,7-dimethyl-4<i>H</i>-pyrido[1,2-<i>a</i>]thieno[3,2-<i>e</i>]pyrimidin-9(5<i>H</i>)-one derivatives <b>12a</b> and <b>12b</b>. Furthermore, the reactivity of acetoacetamide derivative <b>3</b> with 2-cyanoacetohydrazide was investigated through refluxing the reactants in dioxane, which subsequently yielded the corresponding cyanoacetamide derivative <b>13</b>. The chemical identity of the newly synthesized compounds was determined by employing infrared spectroscopy (IR), ¹H NMR, and ¹³C NMR techniques. Newly synthesized heterocycles incorporating thiophenes were evaluated for their antioxidant and antimicrobial potentials. Notably, thiophene scaffolds <b>5a</b>, <b>10b</b>, <b>11</b>, and <b>13</b> displayed notable antioxidant and antimicrobial activities.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1075-1090"},"PeriodicalIF":2.0,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932100","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A facile halogen assisted intramolecular cyclization of (E)-3-(substituted benzylidene)-1-(substituted phenyl)pyrrolidine-2,5-dione","authors":"Ganesh B. Deshmukh,&nbsp;Nilesh S. Patil,&nbsp;Anant B. Kanagare,&nbsp;Dattatraya N. Pansare","doi":"10.1002/jhet.4834","DOIUrl":"10.1002/jhet.4834","url":null,"abstract":"<p>A straightforward method for producing pyrrolo-chromenes involved the utilization of a Wittig reaction, where maleimides reacted with ortho-hydroxy benzaldehyde. This reaction yields <i>ortho</i>-hydroxy benzylidine succinimides, which subsequently undergo molecular bromine-induced intramolecular cyclization, resulting in (E)-3-(substituted benzylidine)-1-(substituted phenyl) pyrrolidine-2,5-dione derivatives (<b>6g-n</b>). The traditional reaction methods demonstrates efficient performance when carried out in a DMF solvent. This approach proves to be user-friendly and provides numerous benefits, including reduced reaction duration, increased product yields, and milder operating conditions. The compounds synthesized in this study will be integrated into our biological screening program and any discoveries pertaining to their biological properties will be further investigated and subsequently documented.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1091-1100"},"PeriodicalIF":2.0,"publicationDate":"2024-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of cyclopentane annulated δ-lactams via diazomethane-mediated CC bond cleavage of α-keto N,O-hemiaminals","authors":"Hari Mangeswara Rao Gorle,&nbsp;Satwinder Singh Marok","doi":"10.1002/jhet.4829","DOIUrl":"10.1002/jhet.4829","url":null,"abstract":"<p>Diazomethane-mediated C-C bond cleavage of α-keto <i>N,O</i>-hemiaminals was investigated for the first time. Diazomethane as a reagent result C-C bond cleavage of norbornyl α-keto <i>N,O</i>-hemiaminals, Grob-like fragmentation, lead to the formation of cyclopentane annulated δ-lactams in excellent yields. We have synthesized the precursor norbornyl α-keto <i>N,O</i>-hemiaminal by the nucleophilic displacement of halogen of norbornyl α-diketone with the various amines.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1070-1074"},"PeriodicalIF":2.0,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932093","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Regioselective N1-methylation of 1H-tetrazoles with methyl 2,2,2-trichloroacetimidate","authors":"Sudhakar Reddy Baddam,&nbsp;Sudhakar Kalagara,&nbsp;Srinivas Ganta,&nbsp;Venkata Suresh Ponnuru,&nbsp;Balaraju Vudari,&nbsp;Seshadri Nalla","doi":"10.1002/jhet.4824","DOIUrl":"10.1002/jhet.4824","url":null,"abstract":"<p>An efficient, mild, and regioselective synthesis of substituted 1-methyl-1<i>H</i>-tetrazole using methyl 2,2,2-trichloroacetimidate is described. The substrate scope of the methodology has been established with wide variety of tetrazoles. <i>N</i>1-Methylated tetrazoles were synthesized with high yields (85%–97%).</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1066-1069"},"PeriodicalIF":2.0,"publicationDate":"2024-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932099","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"An improved microwave-assisted facile one-pot synthesis of novel pyrazolylphosphonates via Knoevenagel-phospha-Michael protocol","authors":"Sara Mahdjoub,&nbsp;Chamseddine Derabli,&nbsp;Muhammet Yildirim,&nbsp;Raouf Boulcina,&nbsp;Abdelmadjid Debache","doi":"10.1002/jhet.4825","DOIUrl":"10.1002/jhet.4825","url":null,"abstract":"<p>In this study, a highly effective microwave-assisted method employing a multicomponent domino Knoevenagel/phospha-Michael reaction has been established. This approach facilitates the synthesis of a novel set of pyrazolylphosphonate derivatives in good yields by combining aryl aldehydes with pyrazolones and trialkylphosphites, utilizing piperidine as a Bronsted base catalyst. All pyrazolylphosphonates have been characterized by means of IR, ¹H-NMR, ¹³C-NMR, and HRMS analyses and physical methods. This protocol can be characterized by its eco-friendly nature, exceptional efficiency in terms of product yields, and short reaction times.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1045-1056"},"PeriodicalIF":2.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932013","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Palladium-catalyzed [4 + 2] cycloaddition of sulfamate-derived cyclic imines with γ-methylidene-δ-valerolactones/2-methylidenetrimethylene carbonate","authors":"Ke-Xin Huang,&nbsp;Wen-Jie Wu,&nbsp;Zhao-Yang Chen,&nbsp;Jia Du,&nbsp;Wen-Chao Gao","doi":"10.1002/jhet.4821","DOIUrl":"10.1002/jhet.4821","url":null,"abstract":"<p>A general and useful palladium-catalyzed [4 + 2] cycloaddition of sulfamate-derived cyclic imines with γ-methylidene-δ-valerolactones (or 2-methylidenetrimethylene carbonate) is described. The developed strategy generated diverse sulfamate-fused piperidine derivatives (or sulfamate-fused 1,3-oxazinane rings) in good yields.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1035-1044"},"PeriodicalIF":2.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932097","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of substituted 5-aryl-2,3-dihydropyrazine 1,4-dioxides based on condensation of N,N′-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine) with various arylglyoxals","authors":"Nadezhda A. Bakuleva,&nbsp;Boris V. Lichitsky,&nbsp;Dmitry V. Tsyganov,&nbsp;Andrey N. Komogortsev,&nbsp;Valeriya G. Melekhina,&nbsp;Evgeny V. Tretyakov","doi":"10.1002/jhet.4826","DOIUrl":"10.1002/jhet.4826","url":null,"abstract":"<p>For the first time, a method for the synthesis of 2,3-dihydropyrazine 1,4-dioxide derivatives was devised. The presented approach is based on the reaction of <i>N</i>,<i>N</i>′-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine) with α-ketoaldehydes. A distinctive feature of the proposed protocol is the application of sulfate of the aforementioned bis-hydroxylamine in the considered condensation. The advantages of the newly developed route are a one-step synthetic procedure involving easily available starting materials, atom economy, and simple work-up of the reaction mixture. The structure of one of the obtained products was confirmed by x-ray analysis.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1057-1065"},"PeriodicalIF":2.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140932098","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Deoxygenation of N-heterocyclic N-oxides with Selectfluor and disulfane","authors":"Muhammed Hanifi Çelikoğlu,&nbsp;Sefa Uçar,&nbsp;Bilal Nişancı","doi":"10.1002/jhet.4818","DOIUrl":"10.1002/jhet.4818","url":null,"abstract":"<p>Herein, we describe a metal-free methodology using Selectfluor with disulfane, for the deoxygenation of N-heterocyclic <i>N</i>-oxides (33 examples). This effective, robust, and simple methodology enables the synthesis of various deoxygenated analogues from a wide range of N-heterocyclic <i>N</i>-oxide cores at room temperature in short reaction times with quantitative yields.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1029-1034"},"PeriodicalIF":2.0,"publicationDate":"2024-04-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.4818","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140591861","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"L-proline-based DES in Knoevenagel synthesis of arylidene rhodanines, thiazolidine-2,4-diones, and barbituric derivatives","authors":"Stéphanie Hesse,&nbsp;Jasmine Hertzog,&nbsp;Sandrine Rup-Jacques","doi":"10.1002/jhet.4819","DOIUrl":"10.1002/jhet.4819","url":null,"abstract":"<p>Deep eutectic solvents (DES) are environmentally friendly solvents that prevent the use of toxic organic solvents and have been extensively studied in recent years. However, volatile organic compounds (VOC) are often still used during workup and isolation of products. Here, a zero-VOC strategy for Knoevenagel reaction is reported. (Hetero)aromatic aldehydes are successfully condensed with rhodanine, thiazolidine-2,4-dione TZD, or barbituric acid under mild conditions in an L-proline-based DES and pure compounds are obtained after hydrolysis without any purification. For the less reactive TZD, activation by microwave allows diminution of reaction time from 24 h to just 1 h.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"1015-1023"},"PeriodicalIF":2.4,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140591856","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A facile microwave-mediated method of 1,4-dihydropyridine carboxylates synthesis by multicomponent reaction","authors":"Shravya Pachipulusu,&nbsp;Karuna Sree Merugu,&nbsp;Ramakrishna Rao Bhonsle,&nbsp;Aravind Kurnool","doi":"10.1002/jhet.4817","DOIUrl":"10.1002/jhet.4817","url":null,"abstract":"<p>An innovative green procedure has been devised to prepare derivatives of 1,4-dihydropyridine (1,4-DHP). This method works with a catalyst process using ethanol as solvent under microwave irradiation conditions, enabling swift reactions (&lt;30 min) with impressive yields (90%–96%). It contributes to an environmentally friendly and easily executable process by using the energy efficiency method. Within 30 min, this method underscores ecologically conscious practices and offers simple purification, streamlining the process by omitting column chromatography. This method highlights the efficacy and eco-friendly nature of synthesizing 1,4-DHPs. This method combines four component reactions, utilizing EtOH as the solvent and triethylamine as the catalyst. Furthermore, the product was characterized by diverse spectroscopic analysis.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 6","pages":"1009-1014"},"PeriodicalIF":2.4,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140591860","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}