Journal of Heterocyclic Chemistry最新文献

Temperature-Controlled Cyclization of Anthranilic Acids to 2-Thioxoquinazolin-4-One or Thiazoloquinazolinone Derivatives Under Microwave Irradiation 微波辐射下蒽胺酸温控环化合成2-噻唑喹唑啉-4- 1或噻唑喹唑啉酮衍生物

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-16 DOI: 10.1002/jhet.70229

Julie Jaouen, Christian Bailly, Natacha Carta, Xavier Thuru, Jean-François Goossens, Laurence Goossens

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Synthesis of Substituted 6-Aminothieno[2,3-b]Pyridine-5-Carbonitriles by Multicomponent Condensation of 2-Aminothiophenes With Aldehydes and Malononitrile 2-氨基噻吩与醛和丙二腈多组分缩合合成取代6-氨基噻吩[2,3-b]吡啶-5-碳腈

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Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-07-02 DOI: 10.1002/jhet.70222

Ilya A. Komkov, Boris V. Lichitsky

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Synthesis of 1,5-Disubstituted-1H-Tetrazole-Bis-1,2,3-Triazole Hybrids via a One-Pot Five-Component/Pseudo-Three-Component Reaction Sequence 一锅五组分/伪三组分反应序列合成1,5-二取代- 1h -四唑-双-1,2,3-三唑杂化物

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-07-30 DOI: 10.1002/jhet.70227

Hugo Cervantes-Valencia, Jisell G. Mejía-Reyes, Luis Chacón-García, Alejandro Islas-Jácome, Carlos J. Cortés-García

{"title":"Synthesis of 1,5-Disubstituted-1H-Tetrazole-Bis-1,2,3-Triazole Hybrids via a One-Pot Five-Component/Pseudo-Three-Component Reaction Sequence","authors":"Hugo Cervantes-Valencia, Jisell G. Mejía-Reyes, Luis Chacón-García, Alejandro Islas-Jácome, Carlos J. Cortés-García","doi":"10.1002/jhet.70227","DOIUrl":"https://doi.org/10.1002/jhet.70227","url":null,"abstract":"<div>\u0000 \u0000 A new strategy is described for the first time to synthesize a heterocyclic hybrid system of 1,5-disubstituted-1H-tetrazole-bis-1,2,3-triazoles through a double one-pot sequence. The approach involves (i) a one-pot five-component process to obtain the key 1,5-DS-T-bis-propargyl compounds 11a–n, using propargylamine as an orthogonal reagent, followed by (ii) a pseudo-three-component reaction consisting of a double CuAAC process with aromatic azides to afford the target hybrids 6a–n in moderate yields. The protocol is operationally simple, proceeds under mild reaction conditions, and some products were purified by recrystallization from methanol. Notably, this is the first example of a higher-order multicomponent sequence combined with a classical pseudo-multicomponent reaction, underscoring the synthetic utility of this approach for the rapid assembly of structurally complex hybrid scaffolds relevant to medicinal chemistry. Finally, the feasibility of accessing the target hybrids in a truly one-pot manner was demonstrated starting from propargylamine, with the overall process forming six C–N bonds, one C–C bond, and one N–N bond within a single operation.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 10","pages":"1530-1540"},"PeriodicalIF":2.9,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100708","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}

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Novel Tertiary Amine-Functionalized Selenium Heterocycles: Synthesis, Antibacterial, and Antioxidant Investigations 新型叔胺功能化硒杂环：合成、抗菌和抗氧化研究

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-07-28 DOI: 10.1002/jhet.70226

Bahgat R. M. Hussein, Sham M. M. El-Saghier, Amer A. Amer

{"title":"Novel Tertiary Amine-Functionalized Selenium Heterocycles: Synthesis, Antibacterial, and Antioxidant Investigations","authors":"Bahgat R. M. Hussein, Sham M. M. El-Saghier, Amer A. Amer","doi":"10.1002/jhet.70226","DOIUrl":"https://doi.org/10.1002/jhet.70226","url":null,"abstract":"<div>\u0000 \u0000 A novel three-series of selenium-containing heterocycles (SeCHet) incorporating tertiary amine functionalities, namely N-alkyl selenopyridines (5a–e and 6a–c) and N-alkyl selenopheno[2,3-b]pyridines 7a–d, were successfully synthesized through the reaction of selenium-chloroacetamide scaffold derivatives 3a and 3b with various secondary amines. These compounds were designed based on the well-established biological importance of both selenium-based heterocyclic compounds and amine-containing molecules in biological activities, particularly their antioxidant and antibacterial properties against selected Gram-positive and Gram-negative bacterial strains. Several compounds exhibited promising biological activity, with derivatives containing the diethylamino and piperidine moieties showing enhanced antibacterial effects, particularly against \u0000 Bacillus cereus\u0000 , with an inhibition percentage more than the standard drug (ciprofloxacin). In addition, notable antioxidant activity was observed for selected compounds; the activity of compound 5b was comparable to vitamin C, with an inhibition percentage similar to vitamin C, 74%. Derivatives 6a and 7a showed the highest antioxidant performance, with inhibition rates of 72% and 67%, respectively, indicating the potential of these structures as biologically active agents. Overall, the obtained results highlight the significance of incorporating tertiary amine and selenopyridine functionalities in the development of new compounds with potential pharmaceutical applications.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 10","pages":"1519-1529"},"PeriodicalIF":2.9,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100514","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}

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From α,β-Unsaturated Aldehydes to Six-Membered Heterocycles: Modern Synthesis of Thiazines and Oxazines 从α，β-不饱和醛到六元杂环：噻嗪和恶嗪的现代合成

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-18 DOI: 10.1002/jhet.70235

Ekaterina A. Verochkina, Nadezhda V. Vchislo, Victoria G. Fedoseeva

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Synthesis and Antimalarial Activity of Triazole Hybrids: Recent Developments and Structure–Activity Relationships 三唑类化合物的合成及抗疟活性研究进展及构效关系

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-07-18 DOI: 10.1002/jhet.70224

Lekkala Ravindar, Lekkala Revathi, Yee Ling Lau

{"title":"Synthesis and Antimalarial Activity of Triazole Hybrids: Recent Developments and Structure–Activity Relationships","authors":"Lekkala Ravindar, Lekkala Revathi, Yee Ling Lau","doi":"10.1002/jhet.70224","DOIUrl":"https://doi.org/10.1002/jhet.70224","url":null,"abstract":"<div>\u0000 \u0000 The rise of drug or multidrug resistance in Plasmodia strains has made malaria the most important tropical parasitic disease. To address this issue, new antimalarial drugs must be developed. As a fundamental building block in organic synthesis, materials science, and pharmaceutical chemistry, the triazole scaffold is an essential part of heterocyclic chemistry. Because of their broad chemical properties and potential biological applications, including antimalarial, the synthesis of triazoles has gained significant attention in the field of organic chemistry. This review primarily focuses on the synthesis, the wide range of antimalarial activities of several hybridized 1,2,3-triazoles and 1,2,4-triazoles, and the structure–activity relationships (SAR) reported since 2022, which target various stages of the Plasmodium life cycle. Because of their adaptability, they are extremely efficient against both drug-sensitive and drug-resistant strains of \u0000 P. falciparum\u0000 , making them indispensable resources in areas where resistance is common. Even higher antimalarial effectiveness has been achieved by the synergistic effects of mixing the triazole moiety with additional pharmacophores. This strategy may be able to surpass current resistance mechanisms and offer a more long-lasting way to treat malaria. Triazole hybrid compounds continue to play a significant role in malarial chemotherapy despite the development of numerous antimalarial leads. Researchers can further investigate and innovate in the synthesis, antimalarial evaluation, and structure–activity relationship (SAR) studies of triazoles as pharmaceuticals by including them as crucial components in drug discovery, thereby examining their potential therapeutic importance.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 10","pages":"1476-1508"},"PeriodicalIF":2.9,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100067","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}

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Acid-Catalyzed Recyclization of Aroyl-Containing Thieno[2,3-b]Pyridin-6(5H)-Ones Into Substituted Thieno[2,3-b]Pyrroles 含芳基噻吩[2,3-b]吡啶-6(5H)- 1在取代噻吩[2,3-b]吡咯中的酸催化再循环

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-07-23 DOI: 10.1002/jhet.70225

Anna A. Zholtovskaya, Aida I. Samigullina, Boris V. Lichitsky

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Photochemical Approach to Fused Quinoxaline Derivatives From Allomaltol-Containing Terarylenes With 2-Aminooxazole Bridge Fragment via Trapping of Unstable Cyclopentene-1,2-Dione Intermediates 利用不稳定环戊烯-1,2-二酮中间体捕获含异丙麦醇的环氧芳烯与2-氨基恶唑桥片段融合喹啉衍生物的光化学方法

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/jhet.70232

Alexander V. Migulin, Vasily A. Migulin, Constantine V. Milyutin, Andrey N. Komogortsev

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Electrocatalytic π-System Cycloadditions for Sustainable Heterocycles and Carbocycles Synthesis 可持续杂环和碳环合成的电催化π系环加成

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/jhet.70233

Kanak Kanti Das, Sutapa Dey

{"title":"Electrocatalytic π-System Cycloadditions for Sustainable Heterocycles and Carbocycles Synthesis","authors":"Kanak Kanti Das, Sutapa Dey","doi":"10.1002/jhet.70233","DOIUrl":"https://doi.org/10.1002/jhet.70233","url":null,"abstract":"<div>\u0000 \u0000 Electrocatalytic cycloadditions of π-systems have emerged as versatile and sustainable strategies for constructing structurally diverse carbocycles and heterocycles. By harnessing anodic oxidation or cathodic reduction, these transformations replace stoichiometric chemical oxidants and metal catalysts with electricity as a traceless reagent, enabling environmentally benign, redox-neutral, and atom-economical pathways. Cycloadditions such as [2 + 1], [2 + 2], [2 + 2 + 2], [3 + 2], [4 + 2], and [5 + 2] efficiently generate cyclobutanes, cyclopentanes, cyclohexanes, and fused polycycles, often proceeding via radical-cationic, 1,3-dipolar, or stepwise electron-transfer mechanisms. Mechanistic studies highlight the critical roles of radical stabilization, electrochemical potential, and substrate polarity in dictating chemo-, regio-, and stereoselectivity. Recent advances include multicomponent, cascade, flow-electrochemical, and asymmetric approaches that expand structural complexity while minimizing waste. Collectively, these studies underscore the versatility of electrocatalytic cycloadditions as a green, tunable, and scalable platform for the synthesis of complex carbocyclic and heterocyclic architectures. This review positions π-system electrocatalysis as a unifying and sustainable paradigm for constructing molecules of relevance to pharmaceuticals, agrochemicals, and materials science, highlighting its potential to replace traditional oxidants and metal-based protocols in modern synthetic chemistry.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 10","pages":"1611-1621"},"PeriodicalIF":2.9,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100662","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}

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Synthesis of the Substituted 5-Hydroxy-1,7-Dihydro-6 H-Pyrazolo[3,4-b]Pyridin-6-Ones by Interaction of 5-Aminopyrazoles With Ethyl Bromopyruvate 5-氨基吡唑与溴丙酮酸乙酯相互作用合成取代的5-羟基-1,7-二氢-6 h -吡唑[3,4-b]吡啶-6- 1

IF 2.9 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-18 DOI: 10.1002/jhet.70236

Tatiana A. Kudryavtseva, Boris V. Lichitsky

{"title":"Synthesis of the Substituted 5-Hydroxy-1,7-Dihydro-6\u0000 H-Pyrazolo[3,4-b]Pyridin-6-Ones by Interaction of 5-Aminopyrazoles With Ethyl Bromopyruvate","authors":"Tatiana A. Kudryavtseva, Boris V. Lichitsky","doi":"10.1002/jhet.70236","DOIUrl":"https://doi.org/10.1002/jhet.70236","url":null,"abstract":"<div>\u0000 \u0000 In the present work, we describe the first example of constructing the 3-hydroxypyridin-2(1H)-one core based on the interaction of heterocyclic enamines with ethyl bromopyruvate. Utilizing a wide range of substituted 5-aminopyrazoles as an enamine component we have shown that the considered condensation leads to the formation of pyrazolo[3,4-b]pyridin-6-one derivatives containing a hydroxyl group. Relying on the investigated reaction a general approach to the synthesis of the target bicyclic system was developed. The application of elaborated protocol to a set of diverse 5-aminopyrazoles allowed us to obtain an array of 5-hydroxy-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-ones with yields up to 82%. The undoubted advantages of the presented method are easily available starting materials, atom economy and facile isolation of the final products without chromatographic purification. The structure of the prepared compounds was confirmed employing 1H and 13C NMR spectroscopy, high-resolution mass spectrometry as well as data of X-ray analysis.\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"63 10","pages":"1588-1600"},"PeriodicalIF":2.9,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149100137","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}

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