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Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-29 DOI: 10.1021/acs.joc.4c02569
Peng-Fei Huang, Ying Peng, Jia-Le Fu, Bo Li, Quan Zhou, Yu Liu
{"title":"Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS2","authors":"Peng-Fei Huang, Ying Peng, Jia-Le Fu, Bo Li, Quan Zhou, Yu Liu","doi":"10.1021/acs.joc.4c02569","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02569","url":null,"abstract":"1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report a green electrochemical three-component reaction of amines, amidines, and CS<sub>2</sub> for the effective synthesis of 3,5-disubstituted-1,2,4-thiadiazoles under metal- and oxidant-free conditions. Both aliphatic and aryl amines are well-tolerated at room temperature in a simple undivided cell. A series of 1,2,4-thiadiazoles are prepared with excellent functional groups.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"72 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734485","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Sodium Poly(heptazine imide)-Enabled Oxytrifluoromethylation of Alkenes for the Synthesis of α-CF3 Ketones
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-29 DOI: 10.1021/acs.joc.5c00117
Chen Bao, Xinyu Zhu, Mengying Xu, Ming Hou, Peng Wang, Guanyinsheng Qiu
{"title":"Sodium Poly(heptazine imide)-Enabled Oxytrifluoromethylation of Alkenes for the Synthesis of α-CF3 Ketones","authors":"Chen Bao, Xinyu Zhu, Mengying Xu, Ming Hou, Peng Wang, Guanyinsheng Qiu","doi":"10.1021/acs.joc.5c00117","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00117","url":null,"abstract":"This paper describes a NaPHI-catalyzed oxytrifluoromethylation of olefins under photoirradiation. The reaction is applicable for the synthesis of α-trifluoromethyl ketones, which could be structurally elaborated into an array of useful scaffolds. Mechanistic studies suggested that photoexcited NaPHI* could facilitate the formation of singlet <sup>1</sup>O<sub>2</sub> through an EnT process, thus enabling difunctionalization with trifluoromethyl radical and oxygen radical anion species.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"69 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Cs2CO3-Mediated Annulation of Cyclopropane-1,1-dicarbonitriles with o-Benzenediamines: Access to Substituted 2-Aminoquinoxalines
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-28 DOI: 10.1021/acs.joc.4c03160
Haiwen Li, Xinyi Wan, Wenzhe Cheng, Cunde Wang
{"title":"Cs2CO3-Mediated Annulation of Cyclopropane-1,1-dicarbonitriles with o-Benzenediamines: Access to Substituted 2-Aminoquinoxalines","authors":"Haiwen Li, Xinyi Wan, Wenzhe Cheng, Cunde Wang","doi":"10.1021/acs.joc.4c03160","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03160","url":null,"abstract":"The Cs<sub>2</sub>CO<sub>3</sub>-mediated formal (4 + 2) cascade annulation strategy for the synthesis of 2-aminoquinoxalines has been developed using D–A cyclopropanes and <i>o</i>-benzenediamines as the substrates. The protocol provides an efficient method of accessing a broad range of 2-aminoquinoxaline derivatives in good to excellent yields with good functional-group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143723976","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-27 DOI: 10.1021/acs.joc.4c03183
Yulia Pronina, Alexander Filatov, Stanislav Shmakov, Stanislav Selivanov, Mariya Kryukova, Dar’ya Spiridonova, Alexander Ponyaev, Alexander Stepakov, Vitali Boitsov
{"title":"Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition","authors":"Yulia Pronina, Alexander Filatov, Stanislav Shmakov, Stanislav Selivanov, Mariya Kryukova, Dar’ya Spiridonova, Alexander Ponyaev, Alexander Stepakov, Vitali Boitsov","doi":"10.1021/acs.joc.4c03183","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03183","url":null,"abstract":"An efficient one-pot three-component [3 + 2]-cycloaddition reaction of azomethine ylides, generated in situ from isatins and azetidine-2-carboxylic acid, with different maleimides and itaconimides has been investigated. These reactions afford the corresponding spiro and dispiro[1-azabicyclo[3.2.0]heptanes] in moderate to high yields (up to 93%) with moderate to excellent diastereoselectivities and excellent regioselectivities under mild conditions. The method provides a simple route to the stereoselective synthesis of new polyheterocyclic systems such as 3-spiro[1-azabicyclo[3.2.0]heptane]oxindoles spiro-conjugated or fused to a succinimide moiety. The observed diastereo- and regioselectivity of cycloaddition reactions is reasoned by DFT studies. The antiproliferative effect of the synthesized compounds against cancer cell lines was assessed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713633","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-27 DOI: 10.1021/acs.joc.4c03181
Neeraj Yadav, Prabal Banerjee
{"title":"(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds","authors":"Neeraj Yadav, Prabal Banerjee","doi":"10.1021/acs.joc.4c03181","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03181","url":null,"abstract":"Herein, we present an acid- and base-mediated approach for ring opening of donor–acceptor cyclopropanes (DACs) followed by (3+2) annulation, yielding biologically relevant <i>gem</i>-difluorinated cyclopentenes via α,α-difluoroketone scaffolds. Fluorinated rings are essential building blocks in drug discovery and materials research. This methodology has a broad substrate scope, is scalable, and provides a practical synthetic route to obtain value-added fluorinated compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713749","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-27 DOI: 10.1021/acs.joc.4c03085
Shuting Zhang, Wen Gu, Fei Yang, Limin Ma, Zhichuan Shi, Xiaoxiao Li, Zhigang Zhao
{"title":"A Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides","authors":"Shuting Zhang, Wen Gu, Fei Yang, Limin Ma, Zhichuan Shi, Xiaoxiao Li, Zhigang Zhao","doi":"10.1021/acs.joc.4c03085","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03085","url":null,"abstract":"Organic selenium compounds are important molecules with a wide range of applications in pharmaceuticals, organic materials, catalysis, and other fields. Herein, we report the synthesis of α-selenomethylketones through the reaction of vinyl azides with arylselenols and benzylselenol. This protocol has the advantages of releasing only nitrogen as a benign byproduct, using air as an environmentally friendly initiator, a very short duration, mild reaction conditions, and broad substrate compatibility. The results of exploratory studies show that oxygen in the air is used as the initiator to promote this radical cascade reaction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143723973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Base-Mediated Synthesis of Imidazole-Fused 1,4-Benzoxazepines via 7-exo-dig Cyclizations: Propargyl Group Transformation
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-26 DOI: 10.1021/acs.joc.5c00106
Nalan Korkmaz Cokol, Fevzi Can Inyurt, İpek Öktem, Ertan Sahin, Ozlem Sari, Cagatay Dengiz, Metin Balci
{"title":"Base-Mediated Synthesis of Imidazole-Fused 1,4-Benzoxazepines via 7-exo-dig Cyclizations: Propargyl Group Transformation","authors":"Nalan Korkmaz Cokol, Fevzi Can Inyurt, İpek Öktem, Ertan Sahin, Ozlem Sari, Cagatay Dengiz, Metin Balci","doi":"10.1021/acs.joc.5c00106","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00106","url":null,"abstract":"Herein, we describe the synthesis of a series of imidazole-fused 1,4-benzoxazepines using 7-<i>exo-dig</i> cyclizations. Two sets of substrates, one containing disubstituted alkyne functional groups and the other featuring terminal alkynes, were synthesized by using <i>O</i>-propargylation, Sonogashira cross-coupling, and condensation reactions between aldehydes and <i>o</i>-diaminobenzene. While the disubstituted substrates yielded exocyclic <i>E</i>/<i>Z</i> configured cyclization products smoothly, the reactions involving terminal alkynes resulted in the formation of isomeric products with altered skeletal structures, in addition to the expected 7-<i>exo-dig</i> cyclization products. Density functional theory (DFT) calculations were used to clarify the mechanisms underlying the formation of these products. It is suggested that these unexpected products are formed through a series of intermolecular <i>O</i>-to-<i>N</i>-propargyl transfer reactions, followed by 7-<i>exo-dig</i> cyclization, in accordance with Baldwin’s rules. Furthermore, this study extensively demonstrates the conversion of exocyclic products to endocyclic products through a base-mediated 1,3-H shift.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703660","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Electrophilic Halogenation of Allenoates and 3-Alkynoates: Synthesis of 1,4-Dicarbonyl (E)-3-Haloalkenes and Mechanistic Investigations
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-26 DOI: 10.1021/acs.joc.4c02951
Paru Jamwal, Yumnam Nganthoinganbi, Ming-Kang Tsai, Ramani Gurubrahamam
{"title":"Electrophilic Halogenation of Allenoates and 3-Alkynoates: Synthesis of 1,4-Dicarbonyl (E)-3-Haloalkenes and Mechanistic Investigations","authors":"Paru Jamwal, Yumnam Nganthoinganbi, Ming-Kang Tsai, Ramani Gurubrahamam","doi":"10.1021/acs.joc.4c02951","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02951","url":null,"abstract":"Allenoates traditionally provide halobutenolides upon reaction with halonium ions via electrophile-assisted halolactonization. Herein, an unusual electrophilic halogenation of di- and trisubstituted allenoates and 3-alkynoates is demonstrated with <i>N</i>-halosuccinimides under DABCO promotion. The protocol affords densely functionalized 1,4-dicarbonyl 3-haloalkenes in good yields with excellent (<i>E</i>)-stereoselectivity (up to 83% yield, &gt;20:1 dr). The allenoates are presumed to form γ-haloallenoate intermediates, which further react with halonium ions and provide the desired scaffolds. The role of the nucleophilic base in the unusual transformation is demystified through control experiments and computational studies. The deliverables are identified as good synthons for various synthetic group transformations and valuable targets for biologically active pyridazine scaffolds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703656","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
2-Alkynyl Indole-3-carbonitriles: Synthon for the Regioselective Synthesis of Functionalized 4-Aminocarbazoles
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-26 DOI: 10.1021/acs.joc.4c03163
Debanik Panda, Shivam A. Meena, Manvi Sharma, Deepika Thakur, Akhilesh K. Verma
{"title":"2-Alkynyl Indole-3-carbonitriles: Synthon for the Regioselective Synthesis of Functionalized 4-Aminocarbazoles","authors":"Debanik Panda, Shivam A. Meena, Manvi Sharma, Deepika Thakur, Akhilesh K. Verma","doi":"10.1021/acs.joc.4c03163","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03163","url":null,"abstract":"An operationally easy and atom-economical approach for the regioselective tandem synthesis of functionalized 4-aminocarbazoles from easily accessible 2-alkynyl indole-3-carbonitriles under mild reaction conditions has been developed. The developed chemistry involves aza-Henry and successive regioselective annulation to afford the functionalized carbazoles. Replacement of nitromethane with acetophenone led to the formation of the corresponding amino(phenyl)methanone-substituted carbazoles, further extending the diversity of the developed chemistry. The developed methodology accommodates wide functional group variation on the alkyne and is successfully applied for late-stage modification of bioactive molecules.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703658","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Mechanistic Study on the Asymmetric Cascade Michael Addition of Alkynone and Oxindole Catalyzed by Chiral Guanidine
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-26 DOI: 10.1021/acs.joc.5c00008
Haoze Li, Cefei Zhang, Changwei Hu, Zhishan Su
{"title":"Mechanistic Study on the Asymmetric Cascade Michael Addition of Alkynone and Oxindole Catalyzed by Chiral Guanidine","authors":"Haoze Li, Cefei Zhang, Changwei Hu, Zhishan Su","doi":"10.1021/acs.joc.5c00008","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00008","url":null,"abstract":"Density functional theory (DFT) calculations with the M06-2X-D3 functional were used to get the mechanistic investigation and stereoselectivity of the cascade Michael addition of alkynone and oxindole, catalyzed by a chiral guanidine-amide compound. The reaction proceeded through a two-step synergistic process involving sequential C–C and C–O bond formation, together with an H-shift. Because of the high energy barriers of 33.5 kcal mol<sup>−1</sup> (for C–C bond construction) and 41.3 kcal mol<sup>–1</sup> (for C–O bond construction), the reaction was difficult to proceed without the catalyst. The guanidine catalyst facilitated the generation of enolized oxindole species with high nucleophilicity, activating both the enolate oxindole and the alkynone via ion-pairing and multiple hydrogen bonding, significantly lowering the activation barriers. The combination of the guanidine unit and the sulfonamide backbone created an excellent semiclosed chiral environment, promoting asymmetric induction. Due to steric effects from the <i>ortho</i>- and <i>para</i>-substituted <i>i</i>Pr groups in SO<sub>2</sub>Ar, the bulky Cy group, and the chiral backbone, the <i>SS</i>-configuration spirocyclization product with high enantio- and diastereoselectivity was formed predominantly. The <i>E</i>/<i>Z</i> selectivity in the formation of the key α,β-unsaturated ketone intermediate was influenced by catalyst-substrate interactions. Extension of the alkyl chain at the 3-position in the oxindole substrate led to the C–O bond formation more difficult, hindering the construction of spirooxindoles.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703659","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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