ACS Organic & Inorganic Au最新文献_第9页

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-02-05

Hunter O. Ford, Brian L. Chaloux, Nishani K. Jayakody, Christopher A. Klug, Eric G. Ruzicka, Meghanne Tighe, Ryan H. DeBlock, Jeffrey W. Long, Debra R. Rolison and Megan Bourg Sassin*,

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IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-02-05

Mahika Luthra, Abril C. Castro*, David Balcells, Kim Daasbjerg and Ainara Nova*,

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IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-02-05

Andreu Tortajada, and , Eva Hevia*,

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IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-02-05

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Rearrangement Cascade Initiated by Nucleophilic Benzyne Attack on 3,6-Di(2-pyridyl)-1,2-diazines. 亲核苯基攻击3,6-二（2-吡啶基）-1,2-嘧啶引发的重排级联。

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-01-28 eCollection Date: 2025-04-02 DOI: 10.1021/acsorginorgau.4c00070

Johannes Schöntag, Theresa Hettiger, William Roberts, Marcus Scheele, Markus Ströbele, Holger F Bettinger

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Rearrangement Cascade Initiated by Nucleophilic Benzyne Attack on 3,6-Di(2-pyridyl)-1,2-diazines 亲核苯基攻击3,6-二（2-吡啶基）-1,2-嘧啶引发的重排级联

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-01-27 DOI: 10.1021/acsorginorgau.4c0007010.1021/acsorginorgau.4c00070

Johannes Schöntag, Theresa Hettiger, William Roberts, Marcus Scheele, Markus Ströbele and Holger F. Bettinger*,

{"title":"Rearrangement Cascade Initiated by Nucleophilic Benzyne Attack on 3,6-Di(2-pyridyl)-1,2-diazines","authors":"Johannes Schöntag, Theresa Hettiger, William Roberts, Marcus Scheele, Markus Ströbele and Holger F. Bettinger*, ","doi":"10.1021/acsorginorgau.4c0007010.1021/acsorginorgau.4c00070","DOIUrl":"https://doi.org/10.1021/acsorginorgau.4c00070https://doi.org/10.1021/acsorginorgau.4c00070","url":null,"abstract":"Aryne intermediates in synthetic organic chemistry offer versatile routes to complex heterocyclic structures that are valuable in pharmaceuticals and materials science. We present a one-step aryne-mediated reaction to synthesize pyrido[1,2-a]indoles interconnected through vinylene or 1,2-phenylene linkers to pyridotriazoles using 2-pyridyl-substituted pyridazines and phthalazines as confirmed via single-crystal X-ray crystallography and NMR spectroscopy. This unexpected rearrangement proceeds under mild conditions. Considering that five bonds are broken and three new bonds are formed in the reaction between 3,6-di-2-pyridyl-1,2,4,5-tetrazine and benzyne, the yield of 16% is fair. Electron-rich substituents on aryne precursors destabilized the products, while electron-deficient substituents offered some stability improvements. DFT studies could reveal the mechanism of this rearrangement.","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 2","pages":"97–104 97–104"},"PeriodicalIF":3.3,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.4c00070","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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-Heterocyclic Carbene-Borane Adducts with Chiral (R)-Chloroethyl and Vinyl Substituents. 手性(R)-氯乙基和乙烯基取代的n -杂环碳硼烷加合物。

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-01-17 eCollection Date: 2025-04-02 DOI: 10.1021/acsorginorgau.4c00088

Germán Rodríguez-López, Tayde O Villaseñor-Granados, Sonia Sánchez-Ruiz, Adriana Esparza-Ruiz, Angelina Flores-Parra

{"title":"N-Heterocyclic Carbene-Borane Adducts with Chiral (R)-Chloroethyl and Vinyl Substituents.","authors":"Germán Rodríguez-López, Tayde O Villaseñor-Granados, Sonia Sánchez-Ruiz, Adriana Esparza-Ruiz, Angelina Flores-Parra","doi":"10.1021/acsorginorgau.4c00088","DOIUrl":"10.1021/acsorginorgau.4c00088","url":null,"abstract":"This research provides how chiral imidazolium salts {1,3-bis[1'-chloro-1'-phenylpropan-2'-yl]-imidazolium} (1a) and enantiopure {1,3-bis[(R)-1-chlorobutan-2-yl]-imidazolium} [1b] can be utilized in diverse synthetic pathways to obtain new carbene-borane adducts (2a-2d): {1,3-bis[1'-chloro-1'-phenylpropan-2'-yl]-imidazolyl-2-ylidene-borane} (2a), {1,3-bis[(Z)-1'-phenylpropen-2'-yl]-imidazolyl-2-ylidene-borane} (2b), {1,3-bis[(R)-1-chlorobutan-2-yl]-imidazolyl-2-ylidene-borane} (2c), and {1,3-bis[but-1-en-2-yl]-imidazolyl-2-ylidene-borane} (2d). The carbene-borane adducts were synthesized and characterized by 13C, 1H, and 11B nuclear magnetic resonance spectroscopy and time-of-flight mass spectrometry. The X-ray crystal analyses of compounds 2a and 2b were performed, and to understand the structure and interactions of 2a, a computational study was carried out. The effect of N-substituents in the NHC-borane adducts was clearly observed in the C-B bond lengths obtained by single-crystal X-ray diffraction, where the C-B bond is longer for adducts with N-(R)-chloroethyl substituents than for vinyl substituents. The analysis of the reduced density gradient and the bond critical point calculations of 2a showed intramolecular proton-hydride and Cl···N interactions. These chiral imidazolium salts could have applicability in the development of new materials and possibly in pharmaceutical research.","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 2","pages":"136-143"},"PeriodicalIF":3.3,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11969273/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143796302","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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-Heterocyclic Carbene-Borane Adducts with Chiral (R)-Chloroethyl and Vinyl Substituents 手性(R)-氯乙基和乙烯基取代的n -杂环碳硼烷加合物

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2025-01-16 DOI: 10.1021/acsorginorgau.4c0008810.1021/acsorginorgau.4c00088

Germán Rodríguez-López, Tayde O. Villaseñor-Granados, Sonia Sánchez-Ruiz, Adriana Esparza-Ruiz* and Angelina Flores-Parra*,

{"title":"N-Heterocyclic Carbene-Borane Adducts with Chiral (R)-Chloroethyl and Vinyl Substituents","authors":"Germán Rodríguez-López, Tayde O. Villaseñor-Granados, Sonia Sánchez-Ruiz, Adriana Esparza-Ruiz* and Angelina Flores-Parra*, ","doi":"10.1021/acsorginorgau.4c0008810.1021/acsorginorgau.4c00088","DOIUrl":"https://doi.org/10.1021/acsorginorgau.4c00088https://doi.org/10.1021/acsorginorgau.4c00088","url":null,"abstract":"This research provides how chiral imidazolium salts {1,3-bis[1′-chloro-1′-phenylpropan-2′-yl]-imidazolium} (1a) and enantiopure {1,3-bis[(R)-1-chlorobutan-2-yl]-imidazolium} [1b] can be utilized in diverse synthetic pathways to obtain new carbene-borane adducts (2a–2d): {1,3-bis[1′-chloro-1′-phenylpropan-2′-yl]-imidazolyl-2-ylidene-borane} (2a), {1,3-bis[(Z)-1′-phenylpropen-2′-yl]-imidazolyl-2-ylidene-borane} (2b), {1,3-bis[(R)-1-chlorobutan-2-yl]-imidazolyl-2-ylidene-borane} (2c), and {1,3-bis[but-1-en-2-yl]-imidazolyl-2-ylidene-borane} (2d). The carbene-borane adducts were synthesized and characterized by 13C, 1H, and 11B nuclear magnetic resonance spectroscopy and time-of-flight mass spectrometry. The X-ray crystal analyses of compounds 2a and 2b were performed, and to understand the structure and interactions of 2a, a computational study was carried out. The effect of N-substituents in the NHC-borane adducts was clearly observed in the C–B bond lengths obtained by single-crystal X-ray diffraction, where the C–B bond is longer for adducts with N-(R)-chloroethyl substituents than for vinyl substituents. The analysis of the reduced density gradient and the bond critical point calculations of 2a showed intramolecular proton–hydride and Cl···N interactions. These chiral imidazolium salts could have applicability in the development of new materials and possibly in pharmaceutical research.","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"5 2","pages":"136–143 136–143"},"PeriodicalIF":3.3,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.4c00088","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745972","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Strategic Methodologies for Efficient Synthesis of Imidazo[1,5-a]pyridine and Benzazepine Analogs via the Unique Ritter-Type Reaction 通过独特的ritter型反应高效合成咪唑[1,5-a]吡啶和苯氮平类似物的策略方法

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2024-12-17 DOI: 10.1021/acsorginorgau.4c0007510.1021/acsorginorgau.4c00075

Gunniga Tanomsiri, Suthimon Boonmee, Nattawadee Chaisan, Jumreang Tummatorn*, Charnsak Thongsornkleeb and Somsak Ruchirawat,

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Strategic Methodologies for Efficient Synthesis of Imidazo[1,5-a]pyridine and Benzazepine Analogs via the Unique Ritter-Type Reaction. 通过独特的里特式反应高效合成咪唑并[1,5-a]吡啶和苯并氮杂卓类似物的策略方法。

IF 3.3

ACS Organic & Inorganic Au Pub Date : 2024-12-17 eCollection Date: 2025-04-02 DOI: 10.1021/acsorginorgau.4c00075

Gunniga Tanomsiri, Suthimon Boonmee, Nattawadee Chaisan, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat

引用次数: 0