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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
Total Synthesis of a Rare-Sugar-Enriched O-Antigenic Tetrasaccharide Repeating Unit of Acinetobacter lwoffii EK30A
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1021/acs.joc.5c00074
Supratim Jana, Mrinmoy Manash Bharali, Abhishek Santra
{"title":"Total Synthesis of a Rare-Sugar-Enriched O-Antigenic Tetrasaccharide Repeating Unit of Acinetobacter lwoffii EK30A","authors":"Supratim Jana, Mrinmoy Manash Bharali, Abhishek Santra","doi":"10.1021/acs.joc.5c00074","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00074","url":null,"abstract":"Herein, we communicate a concise synthetic strategy for the first total synthesis of the <i>O</i>-antigenic tetrasaccharide repeating unit of <i>Acinetobacter lwoffii</i> EK30A polysaccharide. The structurally unique tetrasaccharide possesses three consecutive 1,2-<i>cis</i>-glycosidic linkages and two rare sugar units, <i>i</i>.<i>e</i>., <span>d</span>-Fuc<i>p</i>NAc and <span>d</span>-Qui<i>p</i>4NAc. All functionalized monosaccharides were efficiently synthesized from naturally abundant and inexpensive <span>d</span>-galactose to make the synthetic route affordable and convenient. The tetrasaccharide was synthesized using highly stereoselective, convergent (1 + 2 + 1) and carefully optimizing a high-yielding glycosylation strategy.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703665","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
High-Efficiency Light Emitters: 10-(Diphenylphosphoryl)-anthracenes from One-Pot Synthesis Including C–O–P to C–P(═O) Rearrangement
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1021/acs.joc.4c03139
Vivek Vivek, Marek Koprowski, Ewa Różycka-Sokołowska, Marika Turek, Bogdan Dudziński, Krzysztof Owsianik, Łucja Knopik, Piotr Bałczewski
{"title":"High-Efficiency Light Emitters: 10-(Diphenylphosphoryl)-anthracenes from One-Pot Synthesis Including C–O–P to C–P(═O) Rearrangement","authors":"Vivek Vivek, Marek Koprowski, Ewa Różycka-Sokołowska, Marika Turek, Bogdan Dudziński, Krzysztof Owsianik, Łucja Knopik, Piotr Bałczewski","doi":"10.1021/acs.joc.4c03139","DOIUrl":"https://doi.org/10.1021/acs.joc.4c03139","url":null,"abstract":"We report a one-pot synthesis of 10-(diphenylphosphoryl)-anthracenes, featuring a rare multisubstitution on flanking rings with donor–acceptor groups (F, Br, CN, CF<sub>3</sub>, MeO, OCH<sub>2</sub>O) in 24–60% yields. Catalyzed by TMSOTf, the process involves a phosphinite-to-phosphine oxide rearrangement and cyclization. These emitters exhibit excellent photoluminescence quantum yields of up to 95% in both solution and solid states. Postsynthetic anthracene functionalization as well as the optoelectronic effect of substituents, particularly the Ph<sub>2</sub>P═O group, and the aggregation effect in solid on the photophysical properties, were also explored.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"35 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703663","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 Advanced Heat-Resistant Explosive through Regional Isomerization and Intramolecular Integration
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1021/acs.joc.4c02048
Chengchuang Li, Teng Zhu, Jie Tang, Guangbin Cheng, Chuan Xiao, Hongwei Yang
{"title":"An Advanced Heat-Resistant Explosive through Regional Isomerization and Intramolecular Integration","authors":"Chengchuang Li, Teng Zhu, Jie Tang, Guangbin Cheng, Chuan Xiao, Hongwei Yang","doi":"10.1021/acs.joc.4c02048","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02048","url":null,"abstract":"Among all compounds constructed by intramolecular integration, <b>4</b> (<i>T</i><sub>d</sub> = 321 °C, <i>D</i> = 8799 m s<sup>–1</sup>, IS = 35 J) that integrates ortho amino nitro group and tetrazole framework possesses a much better comprehensive performance than most widely used heat-resistant explosive HNS (<i>T</i><sub>d</sub> = 318 °C, <i>D</i> = 7612 m s<sup>–1</sup>, IS = 5 J), which suggest that it might be a candidate for advanced heat-resistant explosive. Compared with <b>8</b>, isomer <b>4</b> shows significant improvement in density, thermal stability and sensitivity, which may be caused by the relatively strong structural aromaticity, hydrogen bond and large face-to-face π–π interaction surfaces strength.","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":"143703661","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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