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Asian Journal of Organic Chemistry最新文献

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Construction of Dihydropyrano[2,3-c]pyrazolone via Photo-induced Wolff Rearrangement/Chiral Isothiourea Catalyzed [4+2] Cyclization Reaction 通过光诱导沃尔夫重排/手性异硫脲催化[4+2]环化反应构建二氢吡喃并[2,3-c]吡唑酮
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-13 DOI: 10.1002/ajoc.202400387
Zhou Zhang, Siyu Shi, Hai Guo, Zhiqiang Shen, Xia Liu, Jinqi Huang, Wenjin Yan
{"title":"Construction of Dihydropyrano[2,3-c]pyrazolone via Photo-induced Wolff Rearrangement/Chiral Isothiourea Catalyzed [4+2] Cyclization Reaction","authors":"Zhou Zhang,&nbsp;Siyu Shi,&nbsp;Hai Guo,&nbsp;Zhiqiang Shen,&nbsp;Xia Liu,&nbsp;Jinqi Huang,&nbsp;Wenjin Yan","doi":"10.1002/ajoc.202400387","DOIUrl":"10.1002/ajoc.202400387","url":null,"abstract":"<p>A photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cycloaddition reaction of pyrazolone derivatives and <i>α</i>-diazoketones was developed, affording the corresponding dihydropyrano[2,3-<i>c</i>]pyrazolone derivatives in moderate to good yields (50–94 %) with satisfactory to excellent diastereoselectivities (&gt;20 : 1 dr, in almost all cases) and enantioselectivities of 31–99 %. This protocol features readily available substrates, mild reaction conditions, and effective construction of vicinal tertiary and quaternary carbon stereocenters.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216921","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Simple and Facile Conjugate Addition of Cyclic and Acyclic 1,3-Diketones to β-Nitrostyrenes 环状和非环状 1,3-二酮与β-硝基苯炔的简单易行共轭加成反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-13 DOI: 10.1002/ajoc.202400355
Dharti Mistry, Nikunjana Benjamin Macwan, Payal Malvi, Dandamudi V. Lenin
{"title":"A Simple and Facile Conjugate Addition of Cyclic and Acyclic 1,3-Diketones to β-Nitrostyrenes","authors":"Dharti Mistry,&nbsp;Nikunjana Benjamin Macwan,&nbsp;Payal Malvi,&nbsp;Dandamudi V. Lenin","doi":"10.1002/ajoc.202400355","DOIUrl":"10.1002/ajoc.202400355","url":null,"abstract":"<p>A simple synthesis of 3-hydroxy-2-(2-nitro-1-arylethyl)cyclohex-2-en-1-ones, 3-hydroxy-5,5-dimethyl-2-(2-nitro-1-arylethyl)cyclohex-2-en-1-ones and 4-hydroxy-3-(2-nitro-1-arylethyl)pent-3-en-2-ones <i>via</i> conjugate addition of cyclic 1,3-diketones, 1,3-cyclohexanedione and 5,5-dimethyl-1,3-cyclohexanedione and acyclic 1,3-diketone, pentane-2,4-dione to β-Nitrostyrenes were reported. This methodology is pleasing with reliability and scalability with gram scale products that can be synthesized.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216918","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Optically Active Cyclam and Its Transformations 光学活性环酰胺的合成及其转化
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-13 DOI: 10.1002/ajoc.202400310
Kazuhiro Yoshida, Yuya Miwa, Yakumo Tojima, Miyuki Takahashi, Daichi Shishido
{"title":"Synthesis of Optically Active Cyclam and Its Transformations","authors":"Kazuhiro Yoshida,&nbsp;Yuya Miwa,&nbsp;Yakumo Tojima,&nbsp;Miyuki Takahashi,&nbsp;Daichi Shishido","doi":"10.1002/ajoc.202400310","DOIUrl":"10.1002/ajoc.202400310","url":null,"abstract":"<p>Cyclam is a well-known example of a polyaza macrocycle. However, there are few reports of its optically active versions. In this study, we synthesized highly symmetric optically active cyclam (<i>S</i>,<i>S</i>,<i>S</i>,<i>S</i>)-5,7,12,14-tetraphenyl-1,4,8,11-tetraazacyclotetradecane, which has four phenyl groups on the cyclam skeleton, and derivatized it in various ways. We were able to synthesize a chiral Cu complex, an <i>N</i>-ethyl derivative, and a dithiourea from this optically active cyclam. The structures of the chiral Cu complex and dithiourea were verified by single-crystal X-ray diffraction analysis.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216917","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Dithiocarbamate-Functionalized Aliphatic Sulfonyl Fluoride via a One-Pot Three-Component Reaction 通过一锅三组份反应合成二硫代氨基甲酸酯官能化脂肪族磺酰氟
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-08 DOI: 10.1002/ajoc.202400269
Heba H. Mohamedy, Eman Fayad, Hanadi A. Katouah, Hua-Li Qin
{"title":"Synthesis of Dithiocarbamate-Functionalized Aliphatic Sulfonyl Fluoride via a One-Pot Three-Component Reaction","authors":"Heba H. Mohamedy,&nbsp;Eman Fayad,&nbsp;Hanadi A. Katouah,&nbsp;Hua-Li Qin","doi":"10.1002/ajoc.202400269","DOIUrl":"10.1002/ajoc.202400269","url":null,"abstract":"<p>An eco-friendly and efficient method was developed for synthesizing a novel class of aliphatic sulfonyl fluorides in a catalyst-free one-pot reaction. The new approach offers a streamlined synthesis for N-(Substituted)-2-(fluorosulfonyl) ethyl carbamodithioates by combining amines, carbon disulfide, with ethenesulfonyl fluoride. The synthesized compounds were obtained in good yields under mild conditions, making this reaction a valuable tool for exploring new chemical transformations.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141929612","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Construction of New Heterocyclic System, Imidazo[4,5-d]thiazolo[4,3-b]oxazole, via Cascade Reaction of Thioglycolurils with α-Bromoketones 通过硫代甘氨酰与α-溴酮的级联反应构建新的杂环系统--咪唑并[4,5-d]噻唑并[4,3-b]恶唑
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-08 DOI: 10.1002/ajoc.202400369
Ekaterina E. Vinogradova, Valentina A. Karnoukhova, Prof. Angelina N. Kravchenko, Dr. Galina A. Gazieva
{"title":"Construction of New Heterocyclic System, Imidazo[4,5-d]thiazolo[4,3-b]oxazole, via Cascade Reaction of Thioglycolurils with α-Bromoketones","authors":"Ekaterina E. Vinogradova,&nbsp;Valentina A. Karnoukhova,&nbsp;Prof. Angelina N. Kravchenko,&nbsp;Dr. Galina A. Gazieva","doi":"10.1002/ajoc.202400369","DOIUrl":"10.1002/ajoc.202400369","url":null,"abstract":"<p>A method for the synthesis of new heterocyclic system representatives, i. e. imidazo[4,5-<i>d</i>]thiazolo[4,3-<i>b</i>]oxazole derivatives, by the reaction of thioglycolurils with α-bromoketones has been developed. The reaction includes a cascade one-pot S-alkylation/nucleophilic addition/ring-opening/ring-closing process. This protocol is compatible with a broad scope of α-bromoketones, diastereoselectively affording diverse products with 3a<i>S</i>*,4a<i>R</i>*,8a<i>R</i>*-imidazo[4,5-<i>d</i>]thiazolo[4,3-<i>b</i>]oxazole core in 40–76 % yields.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141925958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Efficient Cu-Based Mixed Oxides Catalyst for α-Alkylation of Ketones with Alcohols 高效铜基混合氧化物催化剂用于酮与醇的α-烷基化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-27 DOI: 10.1002/ajoc.202400350
Lina Zhang, Denghong Yao, Xue Wang, Dong Zhang
{"title":"Efficient Cu-Based Mixed Oxides Catalyst for α-Alkylation of Ketones with Alcohols","authors":"Lina Zhang,&nbsp;Denghong Yao,&nbsp;Xue Wang,&nbsp;Dong Zhang","doi":"10.1002/ajoc.202400350","DOIUrl":"10.1002/ajoc.202400350","url":null,"abstract":"<p>A series of Cu-based mixed oxides were prepared by calcinations of corresponding CuMgAl-layered double hydroxides precursors at different temperatures with nominal Cu/Mg/Al ratios of 1 : 1 : 2(Cu-LDH-1), 1 : 2 : 1(Cu-LDH-2),1 : 1 : 1(Cu-LDH-3), and 2 : 1 : 1(Cu-LDH-4). The synthesized catalysts were characterized using X-ray diffraction, high-resolution transmission electron microscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, Fourier transform infrared spectroscopy, inductively coupled plasma atomic emission spectroscopy (ICP-AES), and N<sub>2</sub> physisorption analysis techniques. All as-obtained catalysts showed adequate catalytic performance for the α-alkylation of ketones with alcohols through a hydrogen autotransfer mechanism. The catalyst CuMgAl-I-650 (obtained by calcining Cu-LDH-1 at 650 °C) displayed the highest activity and selectivity. Using this catalyst system, a wide range of branched ketones were synthesized in good to excellent isolated yields. Moreover, the catalyst CuMgAl-I-650 could be recycled and reutilized for four cycles without any significant loss of activity and selectivity. This study provides a very simple and inexpensive catalysis based on transition metals, which are in abundance on earth.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784138","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Diastereoselective Synthesis of Meso-1,2-Diarylethane-1,2-Diamines Via Sodium Reduction of Imidazolines 通过钠还原咪唑啉非对映选择性合成中-1,2-二芳基乙烷-1,2-二胺
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-27 DOI: 10.1002/ajoc.202400305
Daniil R. Bazanov, Natalia A. Lozinskaya
{"title":"Diastereoselective Synthesis of Meso-1,2-Diarylethane-1,2-Diamines Via Sodium Reduction of Imidazolines","authors":"Daniil R. Bazanov,&nbsp;Natalia A. Lozinskaya","doi":"10.1002/ajoc.202400305","DOIUrl":"10.1002/ajoc.202400305","url":null,"abstract":"<p>A facile method for the preparation of meso-1,2-diarylethane-1,2-diamines from aromatic aldehydes is disclosed. The stereoselectivity of the protocol is based on the disrotatory electrocyclic ring closure of readily generated diazopentadienes, followed by a SET reduction of the imidazoline fragment by sodium. The method is readily scalable to multi-gram quantities and a wide range of alkoxy and alkyl-phenyl substituents can be synthesized.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784140","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Simple Conversion of Aldoximes to Nitriles Using Thiourea Dioxide 利用二氧化硫脲实现醛肟与腈的简单转化
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-22 DOI: 10.1002/ajoc.202400291
Peidong Song, Zhe Cui, Tingting Meng, Haojie Rong, Mingzhen Mao, Cuifeng Yang
{"title":"A Simple Conversion of Aldoximes to Nitriles Using Thiourea Dioxide","authors":"Peidong Song,&nbsp;Zhe Cui,&nbsp;Tingting Meng,&nbsp;Haojie Rong,&nbsp;Mingzhen Mao,&nbsp;Cuifeng Yang","doi":"10.1002/ajoc.202400291","DOIUrl":"10.1002/ajoc.202400291","url":null,"abstract":"<p>Thiourea dioxide (TDO) has been demonstrated to be an efficient reagent for the transformation of aromatic, heteroaromatic, alkenyl and aliphatic aldoximes to respective nitriles in excellent yields. Furthermore, this method has been applied to the synthesis of fungicide cyazofamid from a commercial precursor using TDO as a pivotal dehydrating and reducing reagent. This new procedure offers simple and easily reproducible technique for nitrile synthesis and highlights the synthetic utility of TDO as a versatile reagent in organic chemistry.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141754076","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Decarboxylative Iodination of Coumarin‐3‐carboxylic Acids: A Facile Access to 3‐Iodocoumarins 香豆素-3-羧酸的脱羧碘化反应：3-碘香豆素的简便获取途径
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-19 DOI: 10.1002/ajoc.202400308
Vandana Thotathil, Naheed Sidiq, Souha Idoudi, Raed Mohammed Al-Zoubi, Mohanad Gh. Shkoor, Abdulilah Dawoud Bani-Yaseen
{"title":"Decarboxylative Iodination of Coumarin‐3‐carboxylic Acids: A Facile Access to 3‐Iodocoumarins","authors":"Vandana Thotathil, Naheed Sidiq, Souha Idoudi, Raed Mohammed Al-Zoubi, Mohanad Gh. Shkoor, Abdulilah Dawoud Bani-Yaseen","doi":"10.1002/ajoc.202400308","DOIUrl":"https://doi.org/10.1002/ajoc.202400308","url":null,"abstract":"A straightforward protocol for the direct conversion of readily available coumarin‐3‐carboxylic acids to the corresponding 3‐iodocoumarins is described herein. Heating acetonitrile solution of coumarin‐3‐carboxylic acids, molecular iodine and potassium hydrogen phosphate resulted in the decarboxylative iodination of coumarin‐3‐carboxylic acids via radical mechanism. Various electron rich and electron poor coumarin‐3‐carboxylic acids were compatible with the established reaction conditions and consequently afforded the corresponding 3‐iodocoumarins in (46‐93%) reaction yields with minimum purification efforts. The formed products serve as valuable precursors to streamline more complex organic compounds incorporating coumarin core.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141739996","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Multi-Dentate Phosphine Ligand Derived from Cyclotetrasiloxane and Its Application in Palladium-Catalyzed Alkoxycarbonylation of Alkenes 环四硅氧烷衍生的多齿膦配体及其在钯催化烯烃烷氧基羰基化中的应用
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-07-18 DOI: 10.1002/ajoc.202400261
Mengli Liu, Fei Xue, Chuanzhi Xu, Fang Wang, Bo Zeng, Zhen Li, Chungu Xia
{"title":"Multi-Dentate Phosphine Ligand Derived from Cyclotetrasiloxane and Its Application in Palladium-Catalyzed Alkoxycarbonylation of Alkenes","authors":"Mengli Liu,&nbsp;Fei Xue,&nbsp;Chuanzhi Xu,&nbsp;Fang Wang,&nbsp;Bo Zeng,&nbsp;Zhen Li,&nbsp;Chungu Xia","doi":"10.1002/ajoc.202400261","DOIUrl":"10.1002/ajoc.202400261","url":null,"abstract":"<p>The development of phosphine ligands continues to be essential for palladium-catalyzed homogeneous carbonylation reactions, particularly in achieving high regioselectivity. In this study, a cyclosiloxane-based multi-dentate phosphine ligand, L1 (V4-4Ph<sub>2</sub>P), characterized by its high thermal stability and oxidation resistance, was synthesized through the radical addition of secondary phosphines to the double bonds of tetravinyltetramethylcyclotetrasiloxane. L1 was then used in the Pd-catalyzed alkoxycarbonylation of a variety of olefins, including terminal and internal alkenes, cyclic alkenes, aromatic terminal alkenes as well as tetra-, tri- and 1,1-disubstituted alkenes to afford the desired esters with moderate to good yields. As elucidated via DFT calculations and in situ IR spectroscopy, the optimum spatial chelation modes and high stability of Pd−H active species were responsible for the enhancement of catalytic efficiency.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141739995","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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