Journal of Heterocyclic Chemistry最新文献_第2页

The Study of Reaction of Hexafluoro-1,4-Napthoquinone With Substituted 5-Aminopyrazoles

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-30 DOI: 10.1002/jhet.4911

Ekaterina N. Kudryavtseva, Boris V. Lichitsky, Andrey N. Komogortsev, Constantine V. Milyutin, Evgeny V. Tretyakov

{"title":"The Study of Reaction of Hexafluoro-1,4-Napthoquinone With Substituted 5-Aminopyrazoles","authors":"Ekaterina N. Kudryavtseva, Boris V. Lichitsky, Andrey N. Komogortsev, Constantine V. Milyutin, Evgeny V. Tretyakov","doi":"10.1002/jhet.4911","DOIUrl":"https://doi.org/10.1002/jhet.4911","url":null,"abstract":"<div>\u0000 \u0000 <p>For the first time, the interaction of perfluoro-1,4-naphthoquinone with various 5-aminopyrazoles was investigated. It was shown that three types of products can be obtained depending on the structure of starting aminopyrazole. For all examples, the substitution of one fluorine atom in quinone moiety was observed. Wherein, in most cases, the starting aminopyrazoles act as a C-nucleophile leading to 2-(5-aminopyrazol-4-yl)-3,5,6,7,8-pentafluoronaphthalene-1,4-diones. At the same time substrates unsubstituted at ring nitrogen atom regiospecifically react at aminogroup resulting in the formation of 2,5,6,7,8-pentafluoro-3-((pyrazol-5-yl)amino)naphthalene-1,4-diones. Besides that, the absence of steric hindrance in the pyrazole unit allowed us to direct the process at nitrogen atom in Position 2 and synthesize zwitter-ionic 3-(5-aminopyrazol-2-ium-2-yl)-5,6,7,8-tetrafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-olates. The structures of two types of obtained products were confirmed by x-ray analysis.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"1932-1941"},"PeriodicalIF":2.0,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862414","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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GaCl3-Catalyzed [3 + 2]-Cycloaddition/Esterification Cascade of Donor–Acceptor Cyclopropanes With Salicylaldehydes for the Synthesis of Tetrahydro-4 H-Furo[3,2-c]Chromen-4-Ones

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-30 DOI: 10.1002/jhet.4917

Zhiping Liu, Jie Pang, Lijie Che, Chunfang Gan, Jianguo Cui, Yanmin Huang

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Practical Copper-Catalyzed Double N-Arylation of Cyclic Diaryliodoniums: Synthesis of 5H-Dibenzo[d, f][1,3]Diazepine, and Benzo[c]Cinnoline Derivatives

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-30 DOI: 10.1002/jhet.4914

Lianji Zhang, Yujuan Wu, Yuhui Zhao, Cuiping Wang, Wanguo Wei, Zhiqiang Zhang

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A New Route for the Synthesis of (Trichloromethyl)Quinazoline-4(1H)-One and (1,2,3-Triazole)-Quinazoline-4(1H)-One Functionalized Derivatives via Copper-Catalyzed One-Pot Multicomponent Reactions

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI: 10.1002/jhet.4899

Manijeh Nematpour

{"title":"A New Route for the Synthesis of (Trichloromethyl)Quinazoline-4(1H)-One and (1,2,3-Triazole)-Quinazoline-4(1H)-One Functionalized Derivatives via Copper-Catalyzed One-Pot Multicomponent Reactions","authors":"Manijeh Nematpour","doi":"10.1002/jhet.4899","DOIUrl":"https://doi.org/10.1002/jhet.4899","url":null,"abstract":"<div>\u0000 \u0000 <p>The synthesis of functionalized (trichloromethyl)quinazoline-4(1<i>H</i>)-one with high yields through a novel three-component intramolecular C<span></span>H activation reaction from trichloroacetonitrile, benzoyl chlorides, and various primary amines is a remarkable achievement in organic chemistry. This strategy offers a direct and efficient route to access complex molecular structures from readily available starting materials. The use of copper (I) as a catalyst and L-proline as a ligand in tetrahydrofuran at room temperature highlights the importance of transition metal catalysis in enabling selective C<span></span>H activation processes. Furthermore, the subsequent transformation of the obtained product with phenylacetylene and sodium azide in the presence of a copper catalyst in water solvent at room temperature demonstrates the versatility of this synthetic approach in accessing new (1,2,3-triazole)-quinazoline-4(1<i>H</i>)-one derivative. The combination of available starting materials, catalytic systems, mild reaction conditions, and ease of purification procedures contributes to the attractiveness of this method for the synthesis of diverse (trichloromethyl)quinazoline-4(1<i>H</i>)-one and (1,2,3-triazole)-quinazoline-4(1<i>H</i>)-one derivative.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 12","pages":"1914-1923"},"PeriodicalIF":2.0,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862356","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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Palladium-Catalyzed Synthesis of Pyrrolo[1,2-α]Pyrazines From N-Phenacyl Pyrrole-2-Carbonitriles and Aryl Boronic Acids 钯催化 N-苯酰基吡咯-2-甲腈和芳基硼酸合成吡咯并[1,2-α]吡嗪类化合物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI: 10.1002/jhet.4898

Hyejun Park, Seunghwan Shim, Hayoung Jeon, Hwayoung Lee, Kiho Lee, Kyeong Lee, Jae Kyun Lee, Hitesh B. Jalani, Yongseok Choi

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Benzenediazonium Tetrafluoroborate-Catalyzed Formal [3 + 3] Cyclization of 4-Hydroxycoumarins With Propargylicalcohols

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI: 10.1002/jhet.4912

Rongxiang Chen, Xingshuo Li, Jutuan Xiao, Mingli Zhu, Aili Sun, Kai-Kai Wang

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Synthesis and Anticancer Evaluation of Tryptanthrin-1,2,3-Triazole Hybrids 胰黄素-1,2,3-三唑杂化物的合成与抗癌评估

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-26 DOI: 10.1002/jhet.4916

C. B. Meenakshy, Sudheendran Leena Sruthi, E. G. Jayasree, Karakkadparambil Sankaran Sandhya, Ani Deepthi

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Syntheses of 2,4-Substituted Quinazolines via One-Pot Three-Component Reactions Based on Manganese Dioxide/tert-Butyl Hydrogen Peroxide Co-Oxidation Using Alcohols 基于二氧化锰/过氧化氢叔丁酯与醇的一锅三组分反应合成 2,4-取代的喹唑啉类化合物

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-25 DOI: 10.1002/jhet.4913

Yihong Wang, Sheng Huang, Xuehua Chen, Haibo Zhu, Zhanggao Le, Zongbo Xie

{"title":"Syntheses of 2,4-Substituted Quinazolines via One-Pot Three-Component Reactions Based on Manganese Dioxide/tert-Butyl Hydrogen Peroxide Co-Oxidation Using Alcohols","authors":"Yihong Wang, Sheng Huang, Xuehua Chen, Haibo Zhu, Zhanggao Le, Zongbo Xie","doi":"10.1002/jhet.4913","DOIUrl":"https://doi.org/10.1002/jhet.4913","url":null,"abstract":"<div>\u0000 \u0000 <p>Quinazolines and their derivatives occur in various natural products and pharmaceuticals, and thus, various methods of synthesizing quinazolines have been explored. They have traditionally been synthesized via two-component reactions, but these strategies often suffer from the unavailability of the starting materials and limited substrate scopes. To overcome these problems, three-component reactions using additional N sources were developed. Aldehydes were initially used in these reactions, but alcohols are greener and less toxic than aldehydes. However, the previously reported methods involving the use of alcohols require the utilization of transition metal catalysts, ultrahigh temperatures, and extended durations. Thus, an efficient, practical method of synthesizing quinazolines using alcohol is desirable. A facile one-pot three-component method of synthesizing quinazolines utilizing alcohols, 2-aminobenzoketones, and ammonium acetate is reported for the first time, using active MnO<sub>2</sub> and <i>tert</i>-butyl hydrogen peroxide (TBHP) as synergistic oxidants. MnO<sub>2</sub> and TBHP play dual roles: First, they oxidize the alcohol to the aldehyde and then facilitate the transformation of the intermediate into the product. During alcohol oxidation, the synergistic effect of MnO<sub>2</sub> and TBHP is particularly evident. The aldehydes generated in situ via alcohol oxidation undergo immediate subsequent reactions, thereby minimizing their volatilization and side reactions, such as oxidation and polymerization.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1882-1890"},"PeriodicalIF":2.0,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642521","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, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5-Imino-7-Aryl-5 H-Thiazolo[3.2-a]Pyrimidine-6-Carbonitrile and Its Derivatives 新型 5-氨基-7-芳基-5 H-噻唑并[3.2-a]嘧啶-6-甲腈及其衍生物的合成、荧光特性、分子对接研究和晶体结构分析

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-25 DOI: 10.1002/jhet.4890

Yousseuf Touati, Mohammed Benabdallah, Ihcen Merabat, Julio A. Sejas, Ridha Hassaine, Ahmed Djafri, Abdelghani Bouchama, Abdelkader Chouaih, M. P. Vázquez-Tato, Noureddine Choukchou-Braham

{"title":"Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5-Imino-7-Aryl-5\u0000 H-Thiazolo[3.2-a]Pyrimidine-6-Carbonitrile and Its Derivatives","authors":"Yousseuf Touati, Mohammed Benabdallah, Ihcen Merabat, Julio A. Sejas, Ridha Hassaine, Ahmed Djafri, Abdelghani Bouchama, Abdelkader Chouaih, M. P. Vázquez-Tato, Noureddine Choukchou-Braham","doi":"10.1002/jhet.4890","DOIUrl":"https://doi.org/10.1002/jhet.4890","url":null,"abstract":"<div>\u0000 \u0000 <p>This study describes a simple, inexpensive, and effective method for the synthesis of new 5-imino-7-aryle-5<i>H</i>-thiazolo[3,2-a]pyrimidine-3-carbonitrile derivatives 4a-e using a green procedure that does not require the use of heat or a base, creating a strategy that meets both economic and environmental demands. Various synthesized products were characterized via diverse techniques such as <sup>1</sup>H-NMR, infrared (FT-IR), Mass spectroscopy (MS), and single crystal X-ray diffraction. Using a fluorescence spectrometer, the 5-imino-7-phenyle-5<i>H</i>-thiazolo[3.2-a]pyrimidine-3-carbonitrile 4a has been tested as a potent fluorescent agent in mixture of DMSO/Water at 10<sup>−4</sup> M in one hand, and on the other hand the results of our fluorescence evaluation studies with metal ions (Pb(II), Ba(II), Cd(II), Ni(II), Mn(II), Hg(II), Zn(II), Fe(II), Co(II), Cu(II), La(II), Cr(III), and Fe(III)) have shown that this compound exhibits a turn-on and turn-off of the fluorescence to 4a compound with these metals, what forms poor to good interaction by these ions. This result represents the emergence of a new potential ligand for the two heavy cations Cd(II) and Pb(II), which are toxic and polluting, and whose detection is currently of high interest. As well, In the molecular docking evaluation study, it was determined that the 4e molecule has an exceptional ability to inhibit the binding energy of the tubulin protein by −9.13 kcal/mmol, compared to other compounds. The results demonstrate the possibilities for a novel oral medication application.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 11","pages":"1870-1881"},"PeriodicalIF":2.0,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642522","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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Synthetic Approaches Toward Imidazo-Fused Heterocycles: A Comprehensive Review 咪唑杂环的合成方法：全面综述

IF 2 3区化学

Journal of Heterocyclic Chemistry Pub Date : 2024-09-24 DOI: 10.1002/jhet.4910

Pragati Kushwaha, Rashi, Ayush Bhardwaj, Danish Khan

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