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Copper-Catalyzed Oxyfluorosulfonylation of β,γ-Unsaturated Oximes with Sulfur Dioxide and Selectfluor for Isoxazoline-Functionalized Aliphatic Sulfonyl Fluorides 铜催化β,γ-不饱和肟与二氧化硫和选择氟的氧氟磺酰化反应，制备异噁唑啉官能化脂肪族磺酰氟
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c00616
Hui-Jie Du, Lin Qi, Zhi-Min Yan, Jia-Li Liu, Wei Li, Li-Jing Wang
{"title":"Copper-Catalyzed Oxyfluorosulfonylation of β,γ-Unsaturated Oximes with Sulfur Dioxide and Selectfluor for Isoxazoline-Functionalized Aliphatic Sulfonyl Fluorides","authors":"Hui-Jie Du, Lin Qi, Zhi-Min Yan, Jia-Li Liu, Wei Li, Li-Jing Wang","doi":"10.1021/acs.joc.4c00616","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00616","url":null,"abstract":"In this report, we describe a copper-catalyzed cascade reaction involving oxygen radical-induced cyclization/SO<sub>2</sub> insertion/fluorination of β,γ-unsaturated oximes with sulfur dioxide and Selectfluor under mild conditions for the synthesis of isoxazoline-functionalized aliphatic sulfonyl fluorides. The synthetic potential of these compounds has been evaluated through diverse SuFEx reactions.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142246038","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
AcOH-Catalyzed Rearrangements of Benzo[e][1,4]diazepin-2(and 3)-ones: Easy Access to 1,4-Dihydroquinazolines and Their Condensed Analogues AcOH 催化的苯并[e][1,4]二氮杂卓-2(和 3)-酮重排：轻松获得 1,4-二氢喹唑啉及其缩合类似物
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01721
Vakhid A. Mamedov, Nataliya A. Zhukova, Victor V. Syakaev, Aidar T. Gubaidullin, Aida I. Samigullina, Tat’yana N. Beschastnova, Darya S. Perevalova, Olga B. Babaeva, Il′dar Kh. Rizvanov, Oleg G. Sinyashin
{"title":"AcOH-Catalyzed Rearrangements of Benzo[e][1,4]diazepin-2(and 3)-ones: Easy Access to 1,4-Dihydroquinazolines and Their Condensed Analogues","authors":"Vakhid A. Mamedov, Nataliya A. Zhukova, Victor V. Syakaev, Aidar T. Gubaidullin, Aida I. Samigullina, Tat’yana N. Beschastnova, Darya S. Perevalova, Olga B. Babaeva, Il′dar Kh. Rizvanov, Oleg G. Sinyashin","doi":"10.1021/acs.joc.4c01721","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01721","url":null,"abstract":"Presented herein is a novel synthesis of new 2-(quinolin-4-yl)-1,4-dihydroquinazoline systems <b>8</b>, in which the acid-catalyzed rearrangement of spiro[benzo[<i>e</i>][1,4]diazepine-3,4′-quinolin]-2(1<i>H</i>)-ones generated <i>in situ</i> from 3-(2-aminophenyl)-5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-2(1<i>H</i>)-ones <b>6</b> with acetone and alkylmethyl ketones has been realized as an important step. An attempt to synthesize isomeric 2-(2-aminophenyl)-5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-3(4<i>H</i>)-one <b>6′a</b> by hydrolysis of the corresponding <i>N</i>-{2-[5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-3(4<i>H</i>)-on-2-yl]phenyl}acetamide <b>5′a</b> led to a new heterocyclic system, 6-methyl-8,13-dihydro-13a<i>H</i>-quinazolino[4,3-<i>b</i>]quinazolin-5-ium 13a-carboxylate <b>14</b>, as a result of an unexpected rearrangement. In addition, it is noteworthy that during the hydrolysis of <i>N</i>-{2-[5<i>H</i>-benzo[<i>e</i>][1,4]diazepin-2(1<i>H</i>)-on-3-yl]phenyl}acetamides <b>5</b>, the not previously described 14-dihydro-5<i>H</i>-14,5a-(epimino[1,2]benzo)benzo[5,6][1,4]diazepin[2,1<i>-b</i>]quinazolin-6(7<i>H</i>)-ones <b>7</b> were unexpectedly obtained.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247234","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
Synthesis of Diverse N-Trifluoromethyl Pyrazoles by Trapping of Transiently-Generated Trifluoromethylhydrazine 通过捕获瞬时生成的三氟甲基肼合成多种 N-三氟甲基吡唑
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01118
Bao Li, Fenglei Xie, Rui Zhang, Yaoyi Wang, Vijaya B. Gondi, Christopher R. H. Hale
{"title":"Synthesis of Diverse N-Trifluoromethyl Pyrazoles by Trapping of Transiently-Generated Trifluoromethylhydrazine","authors":"Bao Li, Fenglei Xie, Rui Zhang, Yaoyi Wang, Vijaya B. Gondi, Christopher R. H. Hale","doi":"10.1021/acs.joc.4c01118","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01118","url":null,"abstract":"A one-pot synthesis of functionalized <i>N</i>-trifluoromethyl pyrazoles from readily available di-Boc trifluoromethylhydrazine and dialdehydes, diketones, carbonylnitriles, and ketoesters/amides/acids is described. <sup>19</sup>F NMR studies were used to characterize the stability of trifluoromethylhydrazine HCl salt in solution and in solid form and identified a short solution-state half-life of ∼6 h. Optimization of cyclization conditions identified DCM, combined with a strong acid, as a key to suppress the undesired des-CF<sub>3</sub> side products, which formed as a result of the instability of trifluoromethylhydrazine and related intermediates. Despite the short-lived nature of these transient intermediates, their reactivity could be utilized to directly deliver a diverse array of pharmaceutically relevant <i>N</i>-trifluoromethyl pyrazoles in synthetically useful yields.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142246048","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
Mn-Catalyzed Aerobic Oxidative α-Cyanation of Tertiary Amines Using Azo/Hydrazide Redox 利用偶氮/肼氧化还原锰催化叔胺的有氧氧化α-氰化反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01609
Su Been Kim, Gayeong Park, Eun Sun Park, Santanu Maiti, Jinho Kim
{"title":"Mn-Catalyzed Aerobic Oxidative α-Cyanation of Tertiary Amines Using Azo/Hydrazide Redox","authors":"Su Been Kim, Gayeong Park, Eun Sun Park, Santanu Maiti, Jinho Kim","doi":"10.1021/acs.joc.4c01609","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01609","url":null,"abstract":"Azo compounds such as diethyl azodicarboxylate have been used in oxidative coupling reactions to generate iminium ions from tertiary amines. However, the requirement of stoichiometric amounts of azo compounds limits their large-scale applications. Herein, we present an aerobic oxidative α-cyanation of tertiary amines using catalytic amounts of an azo compound or hydrazine. The developed protocol provides a practical and ecofriendly route for α-cyanated tertiary amines, using molecular oxygen as the terminal oxidant.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142246166","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
1O2 and Base Assisted Oxidative Conversion of β-Enaminoesters to α-Acyloxy-β-ketoesters under Visible Light Irradiation 在可见光照射下，1O2 和碱辅助将 β-肉桂酸酯氧化转化为 α-酰氧基-β-酮酯
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01994
Rohit Kumar, Deepak, Nidhi Jain
{"title":"1O2 and Base Assisted Oxidative Conversion of β-Enaminoesters to α-Acyloxy-β-ketoesters under Visible Light Irradiation","authors":"Rohit Kumar, Deepak, Nidhi Jain","doi":"10.1021/acs.joc.4c01994","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01994","url":null,"abstract":"Singlet oxygen (<sup>1</sup>O<sub>2</sub>) and base assisted conversion of β<i>-</i>enaminoesters to α-acyloxy-β-ketoesters is demonstrated under visible light irradiation. The reaction involves formation of an imine intermediate via ene-type pathway initiated by <sup>1</sup>O<sub>2</sub> followed by base promoted dimerization and hydrolysis steps. The method is mild, environmentally friendly, requires air as the oxidant, and gives the products in moderate to high yields.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142246044","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
Phototriggered Self-Catalyzed Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diarylphosphine Oxides in EtOH 3,4-Dihydroquinoxalin-2(1H)-ones with Diarylphosphine Oxides in EtOH 的光诱导自催化磷酸化反应
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-19 DOI: 10.1021/acs.joc.4c01184
Yan-Fang Jiang, Wen-Tao Ouyang, Hong-Tao Ji, Jia-Cheng Hou, Ting Li, Qing-Xia Luo, Chao Wu, Li-Juan Ou, Wei-Min He
{"title":"Phototriggered Self-Catalyzed Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diarylphosphine Oxides in EtOH","authors":"Yan-Fang Jiang, Wen-Tao Ouyang, Hong-Tao Ji, Jia-Cheng Hou, Ting Li, Qing-Xia Luo, Chao Wu, Li-Juan Ou, Wei-Min He","doi":"10.1021/acs.joc.4c01184","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01184","url":null,"abstract":"A highly effective external photocatalyst- and additive-free method for the phosphorylation of 3,4-dihydroquinoxalin-2(1<i>H</i>)-ones to produce phosphorylated dihydroquinoxalin-2(1<i>H</i>)-ones has been reported. A wide variety of phosphorylated products were formed in good to excellent yields. Preliminary mechanistic studies reveal that the phosphorylation process involves an EnT process, a SET process, a HAT process, and a deprotonation process.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247227","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
Synthesis of α,α-Difluoromethylene Amines from Thioamides Using Silver Fluoride 使用氟化银从硫酰胺合成 α,α-二氟亚甲胺
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01752
Haixia Song, Qin Wang, Xiaoying Wang, Yu Pan, Jing Li, Xin-Hua Duan, Mingyou Hu
{"title":"Synthesis of α,α-Difluoromethylene Amines from Thioamides Using Silver Fluoride","authors":"Haixia Song, Qin Wang, Xiaoying Wang, Yu Pan, Jing Li, Xin-Hua Duan, Mingyou Hu","doi":"10.1021/acs.joc.4c01752","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01752","url":null,"abstract":"We developed a mild, rapid process employing AgF and thioamides to produce α,α-difluoromethylene amines efficiently. This method exhibited remarkable tolerance toward various functional groups present in <i>N</i>-sulfonylthioamides, thereby broadening the scope of difluoromethylene sulfonamides through a straightforward approach. Additionally, we applied this approach to synthesize various perfluoroalkyl amines, establishing practical synthetic routes for exploring these compounds in pharmaceutical chemistry and materials science.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142237301","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
Spokewise Total Syntheses of Four Erythrina Alkaloids and Telescoped Syntheses of Six Additional Alkaloids 四种刺五加生物碱的全合成和另外六种生物碱的远距离合成
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01537
Yue-Hong Hu, Zhang-Yan Gan, Qin-Tong Li, Yu-Ting Chen, Meng-En Chen, Ling-Hui Zhang, Jin-Chi Zou, Fu-Min Zhang
{"title":"Spokewise Total Syntheses of Four Erythrina Alkaloids and Telescoped Syntheses of Six Additional Alkaloids","authors":"Yue-Hong Hu, Zhang-Yan Gan, Qin-Tong Li, Yu-Ting Chen, Meng-En Chen, Ling-Hui Zhang, Jin-Chi Zou, Fu-Min Zhang","doi":"10.1021/acs.joc.4c01537","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01537","url":null,"abstract":"Based on rich sulfur-involving chemical transformations, a novel spokewise synthetic strategy, a subclass of the collective strategies, has been developed to concisely synthesize four erythrina alkaloids through a single-step transformation from a common synthetic precursor. Moreover, six additional erythrina alkaloids have also been synthesized by subsequent 1–2 steps chemical transformations. The current synthetic approaches provide a valuable platform for collective total syntheses of erythrina alkaloids and <i>pseudo</i>-natural erythrina alkaloids.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142237303","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
Deciphering Asymmetric Brønsted Base-Aminocatalytic Mode in Pudovik/[1,2]-Phospha-Brook Rearrangement/Michael Cascade Reaction 解密普多维克/[1,2]-磷杂-布鲁克重排/迈克尔级联反应中的不对称布氏碱-氨基催化模式
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01570
Ravneet Kaur, Saurabh Singh Rautela, Mubarik Ali, Ravi P. Singh
{"title":"Deciphering Asymmetric Brønsted Base-Aminocatalytic Mode in Pudovik/[1,2]-Phospha-Brook Rearrangement/Michael Cascade Reaction","authors":"Ravneet Kaur, Saurabh Singh Rautela, Mubarik Ali, Ravi P. Singh","doi":"10.1021/acs.joc.4c01570","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01570","url":null,"abstract":"An approach involving the use of a bifunctional aminocatalyst containing Brønsted base and iminium activation sites for asymmetric multicomponent reactions involving [1,2]-phospha-Brook rearrangement has yet to be realized. Herein, we present an aminocatalytic enantioselective conjugate addition of α-phosphonyloxy enolates formed <i>via</i> [1,2]-phospha-Brook rearrangement to α,β-unsaturated ketones. The methodology unfolds a simple one-pot operation consisting of a robust additive-free catalytic system providing a series of oxindole derivatives having two contiguous stereocenters in high yields with excellent stereoselectivities.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142237096","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
Synthesis of Tetrasubstituted Enamines Using Secondary Amines and In Situ-Generated Allenes from Nitrocyclopropanes 利用仲胺和硝基环丙烷原位生成的烯烃合成四代烯胺
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c00829
Zhong-Yang Xu, Jian-Sheng Wei, Li Liu, Qing-Bo Hu, Jin-Yao Zhu, Zhan-Yu Zhou, Ai-Bao Xia, Dan-Qian Xu
{"title":"Synthesis of Tetrasubstituted Enamines Using Secondary Amines and In Situ-Generated Allenes from Nitrocyclopropanes","authors":"Zhong-Yang Xu, Jian-Sheng Wei, Li Liu, Qing-Bo Hu, Jin-Yao Zhu, Zhan-Yu Zhou, Ai-Bao Xia, Dan-Qian Xu","doi":"10.1021/acs.joc.4c00829","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00829","url":null,"abstract":"A novel reaction of cyclic and acyclic secondary amines with in situ-generated allene intermediate species from nitro-substituted donor–acceptor cyclopropanes is reported. In the presence of a simple inorganic base, NaOH, tetrasubstituted enamine derivatives can be obtained in moderate to excellent yields. The reaction is operationally easy, features mild reaction conditions and simple inorganic bases, and is free of transition metals.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247230","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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