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Journal of Heterocyclic Chemistry最新文献

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Synthesis, Crystal Structure, Molecular Docking, and Molecular Dynamics Simulations of 2,5-Substituted Pyrazolo[4′,3′:5,6]Pyrano[2,3-d]Pyrimidines as Selective Ligands for Adenosine A1 and A2A Receptors 2,5-取代吡唑啉[4 ',3 ':5,6]吡喃[2,3-d]嘧啶作为腺苷A1和A2A受体的选择性配体的合成、晶体结构、分子对接和分子动力学模拟
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-07-02 DOI: 10.1002/jhet.70004
Younesse Ait Elmachkouri, Ezaddine Irrou, Aravazhi Amalan Thiruvalluvar, Olivier Blacque, Venkatramanan Varadharajan, Hassan Ouachtak, Lhoussaine El Ghayati, El Hassane Anouar, Joel T. Mague, El Mokhtar Essassi, Nada Kheira Sebbar, Mohamed Labd Taha
{"title":"Synthesis, Crystal Structure, Molecular Docking, and Molecular Dynamics Simulations of 2,5-Substituted Pyrazolo[4′,3′:5,6]Pyrano[2,3-d]Pyrimidines as Selective Ligands for Adenosine A1 and A2A Receptors","authors":"Younesse Ait Elmachkouri,&nbsp;Ezaddine Irrou,&nbsp;Aravazhi Amalan Thiruvalluvar,&nbsp;Olivier Blacque,&nbsp;Venkatramanan Varadharajan,&nbsp;Hassan Ouachtak,&nbsp;Lhoussaine El Ghayati,&nbsp;El Hassane Anouar,&nbsp;Joel T. Mague,&nbsp;El Mokhtar Essassi,&nbsp;Nada Kheira Sebbar,&nbsp;Mohamed Labd Taha","doi":"10.1002/jhet.70004","DOIUrl":"https://doi.org/10.1002/jhet.70004","url":null,"abstract":"<div>\u0000 \u0000 <p>This study focuses on the design of selective ligands targeting A<sub>1</sub> and A<sub>2A</sub> adenosine receptor subtypes, which are part of the G protein-coupled receptor (GPCR) family. A series of novel pyrazolopyranopyrimidine derivatives <b>7–12</b> were synthesized from pyrano[2,3-<i>c</i>]pyrazole-5-carbonitrile <b>1</b>. The structures of the synthesized compounds were confirmed by NMR spectroscopy, and X-ray crystallography was used to validate Compounds <b>2</b> and <b>6</b>. Molecular docking studies were conducted to evaluate their binding affinities for the human adenosine A<sub>1</sub> and A<sub>2A</sub> receptors, with Compounds <b>2</b> and <b>6</b> showing promising interactions. Additionally, density functional theory calculations were employed to optimize molecular geometries, investigate electronic properties, and support the spectral and stability analysis of these compounds. Molecular dynamics (MD) simulations over 100 ns were performed on the receptor–ligand complexes, particularly for Compound <b>2</b>, to assess their stability and dynamic behavior in a biological environment. These findings highlight Compound <b>2</b> as a potential lead for further development as a selective adenosine receptor ligand. The combined synthetic and computational approach offers valuable insights for future drug discovery efforts targeting GPCRs.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 8","pages":"518-534"},"PeriodicalIF":2.0,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144861642","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
Organocatalytic Enantioselective Synthesis of Oxindole-4-Aminopyrazolone Derivatives via Mannich Reaction of 3-Substituted Oxindoles With Pyrazolinone Ketimines 3-取代氧吲哚与吡唑啉酮酮曼尼希反应有机催化对映选择性合成氧吲哚-4-氨基吡唑酮衍生物
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-30 DOI: 10.1002/jhet.70005
María E. Molinero, Sandra Tejedor, Laura Martín, Alicia Maestro, José M. Andrés
{"title":"Organocatalytic Enantioselective Synthesis of Oxindole-4-Aminopyrazolone Derivatives via Mannich Reaction of 3-Substituted Oxindoles With Pyrazolinone Ketimines","authors":"María E. Molinero,&nbsp;Sandra Tejedor,&nbsp;Laura Martín,&nbsp;Alicia Maestro,&nbsp;José M. Andrés","doi":"10.1002/jhet.70005","DOIUrl":"https://doi.org/10.1002/jhet.70005","url":null,"abstract":"<p>The organocatalyzed Mannich reaction between pyrazolinone ketimines and 3-aryl-substituted oxindoles mediated by a hidroquinine-derived squaramide is reported. This method enables the synthesis of a diverse set of oxindole-4-aminopyrazolone derivatives bearing vicinal tetrasubstituted stereocenters, affording products in good yields (up to 95%), with excellent diastereoselectivity (&gt; 20:1) and moderate enantioselectivity (up to 85:15 er) under mild conditions.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 8","pages":"496-504"},"PeriodicalIF":2.0,"publicationDate":"2025-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.70005","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144861928","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
Visible Light Mediated One Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazole 可见光介导的一锅法合成2,5-二取代1,3,4-恶二唑
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-26 DOI: 10.1002/jhet.4950
Satya Narayana Gondu, Shahadat Ahmed, B. Narayana, Madan Kumar S
{"title":"Visible Light Mediated One Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazole","authors":"Satya Narayana Gondu,&nbsp;Shahadat Ahmed,&nbsp;B. Narayana,&nbsp;Madan Kumar S","doi":"10.1002/jhet.4950","DOIUrl":"https://doi.org/10.1002/jhet.4950","url":null,"abstract":"<div>\u0000 \u0000 <p>A one-pot, three-component photo redox process has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives under mild conditions using a catalytic amount of photocatalyst. The method involves the visible light-mediated coupling of isothiocyanates with hydrazines, followed by intramolecular cyclization with the aid of an alkyl halide to form the desired substituted oxadiazole molecule. The method has been optimized for a wide range of substrates and produces moderate to good yields. The simplicity and efficiency of this method make it a useful tool for the synthesis of structurally interesting molecules for various applications.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 8","pages":"490-495"},"PeriodicalIF":2.0,"publicationDate":"2025-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144861689","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
Design, Synthesis, Antimicrobial Evaluation and In Silico Studies of Novel Indole Clubbed Pyrazole Linked 1,2,3-Triazole Derivatives 新型吲哚棒状吡唑- 1,2,3-三唑衍生物的设计、合成、抗菌评价和硅研究
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-19 DOI: 10.1002/jhet.70001
Monil P. Dholariya, Anilkumar S. Patel
{"title":"Design, Synthesis, Antimicrobial Evaluation and In Silico Studies of Novel Indole Clubbed Pyrazole Linked 1,2,3-Triazole Derivatives","authors":"Monil P. Dholariya,&nbsp;Anilkumar S. Patel","doi":"10.1002/jhet.70001","DOIUrl":"https://doi.org/10.1002/jhet.70001","url":null,"abstract":"<div>\u0000 \u0000 <p>A series of novel indole–pyrazole–triazole hybrids <b>(6a–o)</b> was synthesized using a copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry) under microwave irradiation. The target compounds were obtained in good yields from readily available, low-cost starting materials under simple reaction conditions. Structural confirmation of the synthesized compounds was achieved using <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR, and mass spectrometry. The synthesized hybrids were then evaluated for their in vitro antimicrobial activity against bacterial strains \u0000 <i>Bacillus subtilis</i>\u0000 , \u0000 <i>Staphylococcus aureus</i>\u0000 , \u0000 <i>Escherichia coli</i>\u0000 , \u0000 <i>Pseudomonas aeruginosa</i>\u0000 , and fungal strains <i>Aspergillus niger</i> and \u0000 <i>Candida albicans</i>\u0000 . Among all the compounds, <b>6b</b>, <b>6j</b>, <b>6m</b>, and <b>6o</b> demonstrated potent antibacterial activity comparable to the standard drug Chloramphenicol, while compounds <b>6j</b> and <b>6n</b> showed superior antifungal activity compared to Nystatin. The most active compounds were further analyzed through molecular docking studies using Autodock, targeting DNA gyrase (PDB ID: 1KZN) and sterol 14α-demethylase (PDB ID: 5TZ1) proteins. Additionally, ADME properties were assessed to evaluate the pharmacokinetic potential of all synthesized compounds.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 8","pages":"476-489"},"PeriodicalIF":2.0,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144861792","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-Assisted One-Pot Synthesis of 1,5-Benzodiazepine Derivatives Using Novel ZnFe2O4.Cu(OH)2 Magnetic Nanocomposite as Heterogeneous Catalyst and Their Theoretical Studies as Antifungal Agents 新型ZnFe2O4.Cu(OH)2磁性纳米复合材料微波辅助一锅法合成1,5-苯二氮卓类药物及其抗真菌作用的理论研究
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-18 DOI: 10.1002/jhet.4954
Anjaneyulu Bendi, Anirudh Singh Bhathiwal, Aditi Tiwari, G. B. Dharma Rao, Mozhgan Afshari
{"title":"Microwave-Assisted One-Pot Synthesis of 1,5-Benzodiazepine Derivatives Using Novel ZnFe2O4.Cu(OH)2 Magnetic Nanocomposite as Heterogeneous Catalyst and Their Theoretical Studies as Antifungal Agents","authors":"Anjaneyulu Bendi,&nbsp;Anirudh Singh Bhathiwal,&nbsp;Aditi Tiwari,&nbsp;G. B. Dharma Rao,&nbsp;Mozhgan Afshari","doi":"10.1002/jhet.4954","DOIUrl":"https://doi.org/10.1002/jhet.4954","url":null,"abstract":"<div>\u0000 \u0000 <p>Incredible applications of 1,5-benzodiazepine derivatives in the pharmacological and biological world have encouraged us to synthesize the series of novel 2,4-disubstituted-1,5-benzodiazepine derivatives in one pot using reusable ZnFe<sub>2</sub>O<sub>4</sub>.Cu(OH)<sub>2</sub> magnetic nanocomposite as a heterogeneous catalyst under microwave irradiation with a yield range of 70%–93%. The novel ZnFe<sub>2</sub>O<sub>4</sub>.Cu(OH)<sub>2</sub> catalyst was characterized by XRD and TEM. The synthesized 1,5-benzodiazepine derivatives are further investigated for theoretical DFT observations using Spartan-14 software, Autodock Vina, and Discovery Studio software to study their antifungal activity effectiveness towards CaCYP51 (PDB ID-5EQB) protein and observed that almost all compounds exhibit antifungal activity.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 7","pages":"443-457"},"PeriodicalIF":2.0,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144615537","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
Green Synthesis and Unexpected Transformation of New Oxothiazolo[3,2-c]Pyrimidine Carbonitriles 新型氧噻唑[3,2-c]嘧啶碳腈的绿色合成与意外转化
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-18 DOI: 10.1002/jhet.70000
Çağrı Özbil, Muhammet Yıldırım, Havva Acar, Akın Sağırlı
{"title":"Green Synthesis and Unexpected Transformation of New Oxothiazolo[3,2-c]Pyrimidine Carbonitriles","authors":"Çağrı Özbil,&nbsp;Muhammet Yıldırım,&nbsp;Havva Acar,&nbsp;Akın Sağırlı","doi":"10.1002/jhet.70000","DOIUrl":"https://doi.org/10.1002/jhet.70000","url":null,"abstract":"<div>\u0000 \u0000 <p>A swift microwave-assisted Mannich cyclization between enaminocarbonitriles, formaldehyde, and primary amines giving 3-oxothiazolo[3,2-<i>c</i>]pyrimidine carbonitriles in excellent yields is reported. This protocol has some advantages such as atom-economy, highly practical, water-assisted, catalyst- and chromatography-free. Interestingly, some unexpected aryl thiazolidinones were also accessed over a retro-Mannich-cyclization sequence in the reaction of thiazolo[3,2-<i>c</i>]pyrimidine carbonitriles with mercapto acetic acid.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 7","pages":"458-467"},"PeriodicalIF":2.0,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144615332","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 New Route for the Synthesis of Thiazole-Fused Pyrimidinone Derivatives via Regioselective Intramolecular Mitsunobu Reaction 区域选择性分子内Mitsunobu反应合成噻唑-嘧啶酮衍生物的新途径
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-03 DOI: 10.1002/jhet.4956
Ilária M. S. Lins, Sidney G. D. Feitosa, Janaína V. dos Anjos
{"title":"A New Route for the Synthesis of Thiazole-Fused Pyrimidinone Derivatives via Regioselective Intramolecular Mitsunobu Reaction","authors":"Ilária M. S. Lins,&nbsp;Sidney G. D. Feitosa,&nbsp;Janaína V. dos Anjos","doi":"10.1002/jhet.4956","DOIUrl":"https://doi.org/10.1002/jhet.4956","url":null,"abstract":"<p>This study presents a new route for synthesizing thiazole-fused pyrimidinone derivatives through a regioselective intramolecular Mitsunobu reaction. Previous methods used simultaneous bis-alkylation or 2-aminothiazoline as the uronium derivative in ring closure to form the desired products. However, these methodologies can give a mixture of regioisomers, which was not observed in our results. The developed method showed good to moderate chemical yields and can be applied to synthesizing biologically active compounds.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 7","pages":"436-442"},"PeriodicalIF":2.0,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jhet.4956","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144615077","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
N-(Pyridin-2-yl)Amide-Directed, Copper-Mediated Cyanatation of Arene CH Bonds: A New Approach for the Synthesis of 3-(Pyridin-2-yl)Quinazoline-2,4(1H,3H)-Diones N-（吡啶-2-基）酰胺导向、铜介导的芳烃C - H键氰化反应：合成3-（吡啶-2-基）喹唑啉-2,4(1H,3H)-二酮的新方法
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-06-01 DOI: 10.1002/jhet.4953
Ali Nasirpour, Zarrin Ghasemi, Seyed Abolfazl Hosseini-Yazdi, Michal Dusek, Monika Kucerakova
{"title":"N-(Pyridin-2-yl)Amide-Directed, Copper-Mediated Cyanatation of Arene CH Bonds: A New Approach for the Synthesis of 3-(Pyridin-2-yl)Quinazoline-2,4(1H,3H)-Diones","authors":"Ali Nasirpour,&nbsp;Zarrin Ghasemi,&nbsp;Seyed Abolfazl Hosseini-Yazdi,&nbsp;Michal Dusek,&nbsp;Monika Kucerakova","doi":"10.1002/jhet.4953","DOIUrl":"https://doi.org/10.1002/jhet.4953","url":null,"abstract":"<div>\u0000 \u0000 <p>Herein, we report the efficiency of <i>N</i>-(pyridine-2-yl)-amide as a directing group for copper-mediated coupling of arylamide with KOCN to give 3-(pyridin-2-yl)quinazoline-2,4(1<i>H</i>,3<i>H</i>)-dione derivatives. These products were obtained through an intramolecular cyclization of in situ-generated 2-arylisocyanate intermediates. We also identified a bicopperic complex speculated to be a species involved in ortho C<span></span>H activation reactions.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 7","pages":"430-435"},"PeriodicalIF":2.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144615215","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
Synthesis and Application of Azide-Incorporated Copper-Chelating Peptides for Efficient Click Conjugation Reaction 叠氮化铜螯合肽的合成及应用
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-05-27 DOI: 10.1002/jhet.4955
Yuki Sinozaki, Ryota Otani, Hiroki Tanimoto, Takenori Tomohiro
{"title":"Synthesis and Application of Azide-Incorporated Copper-Chelating Peptides for Efficient Click Conjugation Reaction","authors":"Yuki Sinozaki,&nbsp;Ryota Otani,&nbsp;Hiroki Tanimoto,&nbsp;Takenori Tomohiro","doi":"10.1002/jhet.4955","DOIUrl":"https://doi.org/10.1002/jhet.4955","url":null,"abstract":"<div>\u0000 \u0000 <p>Bioorthogonal reactions that rapidly generate stable products in water are powerful tools for the functionalization and analysis of biomolecules of interest. Here, we developed a series of water-soluble copper-chelating azides for rapid copper-catalyzed azide-alkyne [3+2] cycloaddition (CuAAC) reactions. The integrated accelerating ligand, in which introduced an azido group via a linker to a histidine- and methionine-containing peptide, rapidly and quantitatively afford the triazole product. In the application to protein labeling, the apparent rate constant was approximately three orders of magnitude higher than that of tris[(1-benzyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl]amine (TBTA) by changing the trimolecular reaction to a bimolecular reaction, and also by performing it entirely in aqueous solution. The excellent biocompatibility allowed the reaction to proceed almost completely with trace proteins.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 7","pages":"419-429"},"PeriodicalIF":2.0,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144615541","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
Cu(OTf)2 Catalyzed the Reaction of Donor-Acceptor Cyclopropanes With Salicylaldehyde Phenylhydrazones: Synthesis Polycyclic Tetrahydropyridazines Cu(OTf)2催化供体-受体环丙烷与水杨醛苯基腙的反应：合成多环四氢吡啶
IF 2 3区 化学
Journal of Heterocyclic Chemistry Pub Date : 2025-05-23 DOI: 10.1002/jhet.4952
Zhiping Liu, Lijie Che, Jie Pang, Junan Xiao, Xiyan Tang, Chunfang Gan, Jianguo Cui, Yanmin Huang
{"title":"Cu(OTf)2 Catalyzed the Reaction of Donor-Acceptor Cyclopropanes With Salicylaldehyde Phenylhydrazones: Synthesis Polycyclic Tetrahydropyridazines","authors":"Zhiping Liu,&nbsp;Lijie Che,&nbsp;Jie Pang,&nbsp;Junan Xiao,&nbsp;Xiyan Tang,&nbsp;Chunfang Gan,&nbsp;Jianguo Cui,&nbsp;Yanmin Huang","doi":"10.1002/jhet.4952","DOIUrl":"https://doi.org/10.1002/jhet.4952","url":null,"abstract":"<div>\u0000 \u0000 <p>A simple method has been developed to prepare tetrahydro-5H-chromeno[4,3-<i>c</i>]pyridazin-5-ones by reacting donor-acceptor cyclopropane 1,1-dieters with salicylaldehyde phenylhydrazones in the presence of Cu(OTf)<sub>2</sub>, yielding moderate results with excellent diastereoselectivity. Moreover, control experiments revealed that the reaction proceeds via a tandem [3 + 3]-annulation/lactonization mechanism.</p>\u0000 </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"62 5-6","pages":"402-413"},"PeriodicalIF":2.0,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144482086","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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