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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
An Acetic Acid-Promoted Strecker Type Reaction of N,N-Disubstituted Aminomalononitriles: An Efficient Way for the Construction of α-Aminonitriles
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1021/acs.joc.4c02945
Bo-Wen Wang, Yan-Lin Pu, Run-Ze Li, Bai-Yang Li, Hai-Juan Jiao, Yin-Liang Bai, Wen Bao, Ye Zhang, Dao-Yong Zhu, Shao-Hua Wang
{"title":"An Acetic Acid-Promoted Strecker Type Reaction of N,N-Disubstituted Aminomalononitriles: An Efficient Way for the Construction of α-Aminonitriles","authors":"Bo-Wen Wang, Yan-Lin Pu, Run-Ze Li, Bai-Yang Li, Hai-Juan Jiao, Yin-Liang Bai, Wen Bao, Ye Zhang, Dao-Yong Zhu, Shao-Hua Wang","doi":"10.1021/acs.joc.4c02945","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02945","url":null,"abstract":"A Strecker type reaction between aldehydes and readily available <i>N,N</i>-disubstituted aminomalononitriles has been realized for the first time to give an alternative strategy for the synthesis of α-aminonitriles. This reaction features broad substrate scope and the use of water as solvent, and its utility has been supported by the formal synthesis of racemic Clopidogrel and a 3-aminoindole type of compound.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"57 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703664","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
GeCl2-Mediated Ring Contraction toward Endofullerenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1021/acs.joc.5c00217
Shumpei Sadai, Yoshifumi Hashikawa, Yasujiro Murata
{"title":"GeCl2-Mediated Ring Contraction toward Endofullerenes","authors":"Shumpei Sadai, Yoshifumi Hashikawa, Yasujiro Murata","doi":"10.1021/acs.joc.5c00217","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00217","url":null,"abstract":"Germanium(II) dichloride dioxane complex (GeCl<sub>2</sub>·dioxane) is often utilized as a source of molecular germylene, i.e., GeCl<sub>2</sub>, which is known to undergo oxidative 1,4-addition to conjugated substrates. Inspired by this nature resembled to carbenes, we demonstrated a C═C bond formation from two carbonyl moieties engaged in an aromatic macrocycle. This germylene-mediated reaction enables us to realize efficient synthesis of endo[60]fullerenes through the consecutive ring contraction of open-[60]fullerenes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703666","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
Are Gitonic Dications Really Stable and Visible? Revisiting o,o-Diprotonated Dications of the Nitro Group
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1021/acs.joc.4c02241
Yu Kitazawa, Mahiro Hoshino, Daisuke Hashizume, Atsuya Muranaka, Mutsumi Kimura, Masanobu Uchiyama
{"title":"Are Gitonic Dications Really Stable and Visible? Revisiting o,o-Diprotonated Dications of the Nitro Group","authors":"Yu Kitazawa, Mahiro Hoshino, Daisuke Hashizume, Atsuya Muranaka, Mutsumi Kimura, Masanobu Uchiyama","doi":"10.1021/acs.joc.4c02241","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02241","url":null,"abstract":"We revisited the chemistry of gitonic dications of the nitro group using a combination of experimental, spectroscopic, and computational techniques to settle this long-standing dispute over the notion of superelectrophiles. The <i>o,o</i>-diprotonated species, long considered to be exceptionally stable and long-lived, was not spectroscopically detectable in a solution of 1-nitronaphthalene or β-nitrostyrene in trifluoromethanesulfonic acid (TFSA). Further, the addition of a dinuclear dianion based on monocarba-<i>closo</i>-dodecaborate to 1-nitronaphthalene in TFSA gave the <i>o</i>-monoprotonated salt, as determined by single-crystal X-ray analysis, whereas a proton-bridged half-cation was confirmed to be the dominant species in solution.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"215 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695891","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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