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Journal of Heterocyclic Chemistry最新文献

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One pot multicomponent reaction of curcumin: Green synthesis of novel 1,4-dihydropyridine-2,3-dicarboxylates 姜黄素的一锅多组分反应：新型 1,4-二氢吡啶-2,3-二羧酸盐的绿色合成
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-06-12 DOI: 10.1002/jhet.4857
Nasim Khoshlahjeh Motamed, Kambiz Larijani, Elham Pournamdari, Hamid Saeidian, Fariba Zamani Hargalani
{"title":"One pot multicomponent reaction of curcumin: Green synthesis of novel 1,4-dihydropyridine-2,3-dicarboxylates","authors":"Nasim Khoshlahjeh Motamed,&nbsp;Kambiz Larijani,&nbsp;Elham Pournamdari,&nbsp;Hamid Saeidian,&nbsp;Fariba Zamani Hargalani","doi":"10.1002/jhet.4857","DOIUrl":"10.1002/jhet.4857","url":null,"abstract":"<p>In this research, investigation of one-pot multicomponent reactions of (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (curcumin), primary amines, and activated acetylenic compounds in an aqueous medium at room temperature in the presence of catalytic amounts of silica-coated magnetic nanoparticles functionalized by iminodiacetic acid-copper (Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>/IDA-Cu) was studied which was produced 1,4-dihydropyridine-2,3-dicarboxylate in high yields. The advantages of this procedure were easy separation of products and catalyst, high yields of products, reusability of synthesized catalyst, and good rate of reactions.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1306-1313"},"PeriodicalIF":2.0,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141354905","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}
引用次数: 0
Combination of N-amino-1,2,4-triazole and 4-hydroxy-3,5-dinitropyrazole for the synthesis of high performing explosives 结合 N-氨基-1,2,4-三唑和 4-羟基-3,5-二硝基苯吡唑合成高性能炸药
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-06-05 DOI: 10.1002/jhet.4856
Prachi Bhatia, Pooja Jangra, Vikas D. Ghule, Dheeraj Kumar
{"title":"Combination of N-amino-1,2,4-triazole and 4-hydroxy-3,5-dinitropyrazole for the synthesis of high performing explosives","authors":"Prachi Bhatia,&nbsp;Pooja Jangra,&nbsp;Vikas D. Ghule,&nbsp;Dheeraj Kumar","doi":"10.1002/jhet.4856","DOIUrl":"10.1002/jhet.4856","url":null,"abstract":"<p>In an attempt to cultivate energy-stability balance, a series of nitrogen and oxygen-rich high energy density materials were synthesized based on <i>N</i>-substituted 4-hydroxy-3,5-dinitropyrazole and methylene-linked <i>N</i>-amino-1,2,4-bridges. The hydroxy substituent contributed to oxygen content, hydrogen bonding, and tunability via salt formation. On the other hand, the triazole bridge delivered high nitrogen content and thermal stability. All the synthesized compounds were characterized with multinuclear NMR, FTIR, HRMS, and elemental analysis, and their physicochemical and energetic properties were analyzed. Energetic materials <b>1</b>–<b>5</b> showed high detonation performance and adequate overall stabilities. Compound <b>1</b> exhibited higher density (1.84 g/cm<sup>3</sup>) and detonation performance (<i>D</i><sub><i>v</i></sub> = 8103 m/s, <i>P</i> = 26.9 GPa) in comparison to its reported amino derivative.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1299-1305"},"PeriodicalIF":2.0,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141383828","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}
引用次数: 0
Recent advances in TBHP-promoted heterocyclic ring construction via annulation/cyclization TBHP 通过环化/环合促进杂环构建的最新进展
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-06-02 DOI: 10.1002/jhet.4852
Ravi Varala, Vittal Seema, Mohammed Amanullah, Mohammed Mujahid Alam
{"title":"Recent advances in TBHP-promoted heterocyclic ring construction via annulation/cyclization","authors":"Ravi Varala,&nbsp;Vittal Seema,&nbsp;Mohammed Amanullah,&nbsp;Mohammed Mujahid Alam","doi":"10.1002/jhet.4852","DOIUrl":"10.1002/jhet.4852","url":null,"abstract":"<p>One of the most often utilized hydroperoxides in an array of oxidation strategies is <i>tert</i>-butyl hydroperoxide (<sup>t</sup>BuOOH, TBHP). The key reasons for rising utility of TBHP are its low cost, environmental friendliness, high efficiency, and ability to replace hazardous or rare heavy metal oxidants. In this sexennial update, we concisely and critically discussed the applications of TBHP in heterocyclic ring formations starting from 2018 to date. Merits and demerits of its utility, scope of a synthetic organic transformation along with mechanistic logistics are the key features of this review.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1269-1298"},"PeriodicalIF":2.0,"publicationDate":"2024-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141257376","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}
引用次数: 0
Microwave-enhanced heterocyclization: A convenient procedure for 1,5-benzothiazepine using 2-ethoxy ethanol solvent and its antibacterial potential 微波增强杂环化：使用 2-乙氧基乙醇溶剂制备 1,5-苯并硫氮杂卓的简便方法及其抗菌潜力
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-31 DOI: 10.1002/jhet.4823
Gajanan Kottapalle, Dayanand Jadhav, Pravin Poul, Avinash Shinde
{"title":"Microwave-enhanced heterocyclization: A convenient procedure for 1,5-benzothiazepine using 2-ethoxy ethanol solvent and its antibacterial potential","authors":"Gajanan Kottapalle,&nbsp;Dayanand Jadhav,&nbsp;Pravin Poul,&nbsp;Avinash Shinde","doi":"10.1002/jhet.4823","DOIUrl":"10.1002/jhet.4823","url":null,"abstract":"<p>The present research study involves synthesis of 1,5-benzothiazepines has been prepared, derived from chalcones and 2-aminothiophenol in a catalytic amount of piperidine using different solvent conditions under microwave irradiation procedure with the aim to test their antibacterial activity and effect of different solvents in the synthesis. It resulted in good yield of 1,5-benzothiazepines <b>(3a-j)</b> and proved to be an efficient and environmentally benign procedure. The synthesized compounds were characterized by conventional spectral data and screened for their in vitro antibacterial activity against four pathogenic bacteria using agar diffusion method. The traditional classical heating method takes more reaction time. So, in this study, we have tested microwave irradiation process and found that 2-ethoxy ethanol as an alternative solvent in reducing the reaction time (up to 4–6 min.) with high yield as compared with classical method. The synthesized compounds <b>3a</b>, <b>3c</b>, <b>3d</b>, <b>3e</b>, <b>3 h</b>, <b>3i</b>, <b>3j</b> exhibit good to moderate antibacterial activity.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1261-1268"},"PeriodicalIF":2.0,"publicationDate":"2024-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141190681","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}
引用次数: 0
Visible-light photoredox catalyzed synthesis of tetrahydrobenzofuranone: Oxidative [3 + 2] cycloaddition of dicarbonyl and alkene 可见光光氧化催化合成四氢苯并呋喃酮：二羰基与烯烃的氧化[3 + 2]环加成反应
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-29 DOI: 10.1002/jhet.4820
Kartikey, Deepali Jaiswal, Shailesh Singh, Shefali Jaiswal, Mohammad Saquib, Santosh Singh, Surya Pratap Verma, Jaya Singh, Jagdamba Singh
{"title":"Visible-light photoredox catalyzed synthesis of tetrahydrobenzofuranone: Oxidative [3 + 2] cycloaddition of dicarbonyl and alkene","authors":"Kartikey,&nbsp;Deepali Jaiswal,&nbsp;Shailesh Singh,&nbsp;Shefali Jaiswal,&nbsp;Mohammad Saquib,&nbsp;Santosh Singh,&nbsp;Surya Pratap Verma,&nbsp;Jaya Singh,&nbsp;Jagdamba Singh","doi":"10.1002/jhet.4820","DOIUrl":"10.1002/jhet.4820","url":null,"abstract":"<p>Visible-light-mediated formation of tetrahydrobenzofuranone by direct oxidative [3 + 2] cycloaddition via coupling between dimedone and chalcone using eosin-Y as a photoredox catalyst has been reported. The reaction takes place by a radical pathway as evidenced from our experiments and literature. The developed method involves the utilization of visible-light photoredox catalysis for the formation of C-C and C-O bond via abstraction of methylinic hydrogen of dimedone and <i>β</i>-carbon of chalcone as well as coupling between carbonyl group of dimedone and α-carbon of chalcone in tetrahydrobenzofuranone in one-pot procedure. The present protocol shows significant advantages such as the application of visible light as a clean source of energy, green solvent, mild reaction conditions, cost effectiveness, short reaction time, metal free synthesis, easy operation, high atom economy, and broad substrate scope with functional group tolerance. Moreover, outstanding yield of the product obtained up to 82%.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1248-1260"},"PeriodicalIF":2.0,"publicationDate":"2024-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141190324","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}
引用次数: 0
Recyclization of 3-substituted-6,8-dimethylchromones with some heterocyclic enamines: Spectroscopic, quantum calculations (HOMO–LUMO, MEP, NLO), biological evaluation, and ADME investigation 3-取代的-6,8-二甲基色酮与一些杂环烯胺的再环化：光谱、量子计算（HOMO-LUMO、MEP、NLO）、生物评估和 ADME 研究
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-24 DOI: 10.1002/jhet.4827
Al-Shimaa Badran, Magdy A. Ibrahim
{"title":"Recyclization of 3-substituted-6,8-dimethylchromones with some heterocyclic enamines: Spectroscopic, quantum calculations (HOMO–LUMO, MEP, NLO), biological evaluation, and ADME investigation","authors":"Al-Shimaa Badran,&nbsp;Magdy A. Ibrahim","doi":"10.1002/jhet.4827","DOIUrl":"10.1002/jhet.4827","url":null,"abstract":"<p>The chemical reactivity of some 6,8-dimethylchromones was studied toward certain heterocyclic enamines. Treatment of carboxaldehyde <b>1a</b> with the certain enamines proceeded via condensation with concomitant γ-pyrone ring opening. Reaction of carbonitrile <b>1b</b> with enamine derivatives proceeded through opening of γ-pyrone moiety associated with cycloaddition into the nitrile function. A novel angular chromenopyrazolopyridine and chromenopyridopyrimidines were efficiently synthesized from reacting carboxamide <b>1c</b> with the current enamines. Moreover, frontier molecular orbitals analysis, electronegativity, global hardness, global softness, ionization energy, and HOMO-LUMO energy gap were calculated by using DFT/B3LYP/6-311++G(d,p) level. Using the GIAO approach, the <sup>1</sup>H and <sup>13</sup>C NMR spectra were calculated and showed good agreement with the experimental values. Additionally, the nonlinear optical (NLO) properties of the prepared compounds were found higher than urea. MEP was utilized to ascertain reactive sites within the molecules. The produced compounds exhibited varying degrees of inhibitory effect when tested for their antimicrobial and anticancer properties. The evaluation of ADME (absorption, distribution, metabolism, and excretion) parameters indicated good drug-like properties of all the investigated compounds.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1224-1247"},"PeriodicalIF":2.0,"publicationDate":"2024-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141101494","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}
引用次数: 0
A synthetic strategy for the preparation of alkoxy-functionalized bis-1,2,4-triazinyl-2,6-pyridines 制备烷氧基官能化双-1,2,4-三嗪基-2,6-吡啶的合成策略
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-23 DOI: 10.1002/jhet.4828
Mariah L. Tedder, Jesse D. Carrick
{"title":"A synthetic strategy for the preparation of alkoxy-functionalized bis-1,2,4-triazinyl-2,6-pyridines","authors":"Mariah L. Tedder,&nbsp;Jesse D. Carrick","doi":"10.1002/jhet.4828","DOIUrl":"10.1002/jhet.4828","url":null,"abstract":"<p>Heteroaryl-1,2,4-triazine complexants are commonly utilized in separation science for the selective chelation of minor An from Ln in simulated high-level waste. To facilitate access to relevant chemical entities for hypothesis-driven inquiry toward improved separations performance, a synthetic method to construct various alkoxy-complexant derivatives was required. In this work, a convergent synthetic strategy for the production of 3,3′- and 4,4′-tetraalkoxy-bis-1,2,4-triazinyl-2,6-pyridines from readily available starting materials via a dealkylation/alkylation/condensation approach is described. Synthetic method development, substrate scope, preliminary solubility, and hydrolytic stability data in various process-relevant diluents are reported herein.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 8","pages":"1211-1223"},"PeriodicalIF":2.0,"publicationDate":"2024-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141103105","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}
引用次数: 0
Simple and green synthesis of 3-acyl-pyrazolo[1,5-a]pyridines: [3+2] through cycloaddition of N-aminopyridines on enaminones 3-acyl-pyrazolo[1,5-a]pyridines 的简单绿色合成：通过 N-氨基吡啶与烯胺酮的环加成反应实现 [3+2］
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-22 DOI: 10.1002/jhet.4851
Sébastien Redon, Patrice Vanelle
{"title":"Simple and green synthesis of 3-acyl-pyrazolo[1,5-a]pyridines: [3+2] through cycloaddition of N-aminopyridines on enaminones","authors":"Sébastien Redon,&nbsp;Patrice Vanelle","doi":"10.1002/jhet.4851","DOIUrl":"10.1002/jhet.4851","url":null,"abstract":"<p><b>A practicable method is described for the synthesis of 3-acyl-pyrazolo[1,5-<i>a</i>]pyridines from <i>N</i>-aminopyridines and easily available enaminones <i>via</i> a [3+2] cycloaddition. The reactions proceed well with a broad scope, without using additive (base or oxidant).</b></p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1200-1205"},"PeriodicalIF":2.0,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.4851","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141107980","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}
引用次数: 0
2-Vinylaniline in the synthesis of heterocycles: Recent advances 2 乙烯基苯胺在杂环合成中的应用：最新进展
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-21 DOI: 10.1002/jhet.4838
Fatemeh Doraghi, Hamed Navid, Somaye Karimian, Bagher Larijani, Mohammad Mahdavi
{"title":"2-Vinylaniline in the synthesis of heterocycles: Recent advances","authors":"Fatemeh Doraghi,&nbsp;Hamed Navid,&nbsp;Somaye Karimian,&nbsp;Bagher Larijani,&nbsp;Mohammad Mahdavi","doi":"10.1002/jhet.4838","DOIUrl":"10.1002/jhet.4838","url":null,"abstract":"<p>2-Vinylanilines are readily accessible substrates, which are undoubtedly one of the best candidates for the construction of diversely nitrogen-containing heterocyclic compounds. Owing to the amine and alkenyl groups in their structures, these frameworks offer a facile, direct, and selective synthetic method. This review describes various cyclization reactions involving 2-vinylanilines catalyzed by transition metals, or under metal-free conditions.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1180-1199"},"PeriodicalIF":2.0,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141118245","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}
引用次数: 0
A review on pyrimidine-based derivatives: Synthesis and their biological application 嘧啶类衍生物综述：合成及其生物学应用
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2024-05-21 DOI: 10.1002/jhet.4837
Md. Wahidul Islam, Md. Monarul Islam, Rabeya Akter, Tayebur Rahman Limon, Erick S. Vasquez, Md. Aftab Ali Shaikh, Ahsan Habib
{"title":"A review on pyrimidine-based derivatives: Synthesis and their biological application","authors":"Md. Wahidul Islam,&nbsp;Md. Monarul Islam,&nbsp;Rabeya Akter,&nbsp;Tayebur Rahman Limon,&nbsp;Erick S. Vasquez,&nbsp;Md. Aftab Ali Shaikh,&nbsp;Ahsan Habib","doi":"10.1002/jhet.4837","DOIUrl":"10.1002/jhet.4837","url":null,"abstract":"<p>Pyrimidine-based derivatives have attracted a lot of interest in heterocyclic chemistry due to its versatile structure and diverse biological activities. This study provides a comprehensive overview of synthetic strategy of different pyrimidine ring and highlights their biological importance. In this article, we start off by going through the fundamental procedures for the synthesis of pyrimidine scaffolds, including both conventional and contemporary synthetic techniques. These works cover a range of therapeutic domains, such as effects that are anticancer, antibacterial, antiviral, anti-inflammatory, antioxidant, antimalarial, and so on. Moreover, we have summarized with a discussion of future prospects and challenges in the field of pyrimidine heterocyclic chemistry. This thorough review is a significant resource for researchers in medicinal chemistry and related fields since it offers insightful information about the synthetic methods and biological applications of pyrimidine-based derivatives.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 7","pages":"1159-1179"},"PeriodicalIF":2.0,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141117587","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}
引用次数: 0
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