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Elemental Sulfur Promoted Cyclization of o-Chloronitrobenzenes and Aryl Isothiocyanates to Furnish 2-Aminobenzothiazoles 元素硫促进邻氯硝基苯和芳基异硫氰酸酯环化生成 2-氨基苯并噻唑
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-23 DOI: 10.1002/ejoc.202401080
Duyen K. Nguyen, Tran D. B. Pham, Giang T. H. Tran, Phong D. Nguyen, Truong K. Chau, Khanh T. N. Ong, Anh T. Nguyen, Tung Nguyen
{"title":"Elemental Sulfur Promoted Cyclization of o-Chloronitrobenzenes and Aryl Isothiocyanates to Furnish 2-Aminobenzothiazoles","authors":"Duyen K. Nguyen, Tran D. B. Pham, Giang T. H. Tran, Phong D. Nguyen, Truong K. Chau, Khanh T. N. Ong, Anh T. Nguyen, Tung Nguyen","doi":"10.1002/ejoc.202401080","DOIUrl":"https://doi.org/10.1002/ejoc.202401080","url":null,"abstract":"Methods to afford 2-aminobenzothiazoles often involve the use of o-aminothiophenols or aniline-typed precursors. Herein we describe a method to furnish 2-aminobenzothiazoles through the cyclization of o-chloronitrobenzenes and aryl isothiocyanates with the assistance of elemental sulfur. From the perspective of step economy, our strategy allows for the direct use of nitroarene precursors without further reduction to anilines. The scope of the reaction with respect to both substrates was investigated, and it was found that electronic properties of the aryl isothiocyanate was important for obtaining acceptable yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"34 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487868","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Regioselective Synthesis of Thiazole-5-thione Based on [2 + 3] Annulation Trapping of α-Keto Sulfine with Thioamide 基于α-酮硫与硫酰胺的[2 + 3]环化诱捕的噻唑-5-硫酮的区域选择性合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-22 DOI: 10.1002/ejoc.202401056
Xuehua Zhang, Yingxue Lin, Mingyang Guo, Kewen Xu, Jinhui Zhu, Jun Dong
{"title":"Regioselective Synthesis of Thiazole-5-thione Based on [2 + 3] Annulation Trapping of α-Keto Sulfine with Thioamide","authors":"Xuehua Zhang, Yingxue Lin, Mingyang Guo, Kewen Xu, Jinhui Zhu, Jun Dong","doi":"10.1002/ejoc.202401056","DOIUrl":"https://doi.org/10.1002/ejoc.202401056","url":null,"abstract":"Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2 + 3] cyclization reaction of α-keto sulfines generated from the elimination of arylacyl sulfoxides and thioamides. This new strategy allows for the synthesis of thiazole-5-thiones directly without catalysts or additives. The approach features a step-economic, one-pot characteristics via a tandem sequence of in situα-keto sulfines generation, regiospecifically nucleophilic attack or [3 + 2] cyclizatoin, dithioate (S=C−S−) skeletons formation, and subsequent intramolecular nucleophilic cyclization. This reaction also represents a novel method for constructing dithioate (S=C−S−) skeletons.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486477","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 Visible-Light-Induced π-Extension of Perylene Tetraesters: An Investigation on Regioselectivity 可见光诱导的过烯烃四酯的高效π-延伸：区域选择性研究
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-22 DOI: 10.1002/ejoc.202400734
Keisuke Fujimoto, Shingo Miyano, Kenshin Norizuki, Toshiyasu Inuzuka, Tetsuya Sengoku, Masaki Takahashi
{"title":"Efficient Visible-Light-Induced π-Extension of Perylene Tetraesters: An Investigation on Regioselectivity","authors":"Keisuke Fujimoto, Shingo Miyano, Kenshin Norizuki, Toshiyasu Inuzuka, Tetsuya Sengoku, Masaki Takahashi","doi":"10.1002/ejoc.202400734","DOIUrl":"https://doi.org/10.1002/ejoc.202400734","url":null,"abstract":"The present study discloses a highly efficient visible-light-induced π-extension of perylene tetraesters and discussion on the regioselectivity in the photocyclization. We initially found that π-extension reaction of 3,4-dimethoxyphenyl perylene tetraester smoothly proceeded by only irradiating blue LED with a complete regioselectivity. Investigations of the photocyclization with various substrates revealed the relationship between the regioselectivity and electron-donating/withdrawing effects of the substituents on the aromatic groups. Moreover, theoretical investigation suggested the importance of bond alteration in the aromatic groups: cyclization proceeds preferentially at shorter C-C bonds with higher double bond characters. The findings will open new possibilities for the practical synthesis of custom-designed π-extended perylene materials.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486471","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photo-Induced Difluoroethylation or Monofluoromethyl Sulfonylation of 2-Amino Aryl Ethynes to Access Diverse Seven-Membered N-Heterocycles 光诱导 2-氨基芳基乙炔的二氟乙基化或单氟甲基磺酰化反应，以获得多种七元 N-杂环
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-22 DOI: 10.1002/ejoc.202400969
Yunfei Tian, Luping Zheng, Dongyu Guo, Xinping Ding, Weijun Fu, Zejiang Li
{"title":"Photo-Induced Difluoroethylation or Monofluoromethyl Sulfonylation of 2-Amino Aryl Ethynes to Access Diverse Seven-Membered N-Heterocycles","authors":"Yunfei Tian, Luping Zheng, Dongyu Guo, Xinping Ding, Weijun Fu, Zejiang Li","doi":"10.1002/ejoc.202400969","DOIUrl":"https://doi.org/10.1002/ejoc.202400969","url":null,"abstract":"A photo-induced two/three-component radical difluoroethylation or monofluoromethyl sulfonylation of 2-amino aryl ethynes was smoothly finished, which gave a series of difluoroethyl or monofluoromethyl sulfonyl seven-membered N-heterocycles. The two radical systems featured simple/mild reaction conditions, good substrate scopes, and excellent E/Z selectivity. In addition, various radical intermediates were successfully detected by HRMS to explore the reaction process. Single-crystal X-ray diffraction and scaled-up experiments examined the product scaffold and application of this cyclization system.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486826","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 Enamides through Hydro‐Functionalization of Ynamides 通过亚酰胺的氢官能化合成烯酰胺
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400637
Archana Mishra , Subhransu Sekhar Pati , Jaya Prakash Das
{"title":"Synthesis of Enamides through Hydro‐Functionalization of Ynamides","authors":"Archana Mishra ,&nbsp;Subhransu Sekhar Pati ,&nbsp;Jaya Prakash Das","doi":"10.1002/ejoc.202400637","DOIUrl":"10.1002/ejoc.202400637","url":null,"abstract":"<div><div>Most of the methods for the synthesis of functionalized enamides from ynamides were developed in the last two decades showing the contemporary interest in the exploration of ynamide chemistry. The utilization of the intrinsic reactivity of the ynamide triple bond through keteniminium intermediacy, coordination with metals, and as a radical acceptor toward the development of strategies for the synthesis of functionalized enamides reflect the constant strive and creativity in the design and execution of synthetic methods. The present review summarizes the synthetic strategies developed during the last two decades and is divided into the sections depending on the type of hydrofunctionalization reaction. It may be predicted that this field of chemistry will continue to grow exponentially in the coming years and the ready availability of a wide range of ynamides now provides an excellent opportunity to further enrich mainstream synthetic methodologies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 40","pages":"Article e202400637"},"PeriodicalIF":2.5,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141746644","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Palladium‐Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides 钯催化咔唑与炔基溴化物的直接炔基化反应
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400649
Jyothis Dharaniyedath , Vikash Kumar , Parthasarathy Gandeepan
{"title":"Palladium‐Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides","authors":"Jyothis Dharaniyedath ,&nbsp;Vikash Kumar ,&nbsp;Parthasarathy Gandeepan","doi":"10.1002/ejoc.202400649","DOIUrl":"10.1002/ejoc.202400649","url":null,"abstract":"<div><div>Carbazole derivatives are vital in medicinal and materials chemistry, yet accessing diverse substitutions remains challenging. Here, we introduce a regioselective approach for C1 and C8 alkynylation of carbazoles via palladium‐catalyzed C−H activation. This method provides a direct route to mono‐ and di‐alkynylated derivatives, addressing the scarcity of alkynylated carbazole‐based materials. Our study broadens the synthetic toolbox for carbazole functionalization, offering potential applications in optoelectronics, bio‐imaging, and beyond, while contributing to developing sustainable C−H activation methodologies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 40","pages":"Article e202400649"},"PeriodicalIF":2.5,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141334626","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Adaptable Synthesis of Chondroitin Sulfate Disaccharide Subtypes Preprogrammed for Regiospecific O‐Sulfation 为区域特异性 O-硫酸化预设的软骨素硫酸二糖亚型的适应性合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400587
Hannah S. Wootton , Sian S. Berry , Elaine L. Ferguson , Clare S. Mahon , Gavin J. Miller
{"title":"Adaptable Synthesis of Chondroitin Sulfate Disaccharide Subtypes Preprogrammed for Regiospecific O‐Sulfation","authors":"Hannah S. Wootton ,&nbsp;Sian S. Berry ,&nbsp;Elaine L. Ferguson ,&nbsp;Clare S. Mahon ,&nbsp;Gavin J. Miller","doi":"10.1002/ejoc.202400587","DOIUrl":"10.1002/ejoc.202400587","url":null,"abstract":"<div><div>A divergent synthetic route to chondroitin sulfate (CS) disaccharide precursors, including rarer subtypes such as CS−D, has been developed. From common intermediates, a series of thioglycoside D‐glucosyl donors and 4,6‐<em>O</em>‐benzylidene protected D‐galactosamine acceptors are utilised in a robust glycosylation reaction, achieving β‐selectivity and consistent yields (60–75 %) on scales &gt;2.0 g. A post‐glycosylation oxidation to D‐glucuronic acid and orthogonal protecting groups delivers access to CS−A, CS−C, CS−D, CS−E and CS−O precursor subtypes. Of further note is a 4‐<em>O</em>‐benzyl regioselective reductive ring opening of a 4,6‐<em>O</em>‐benzylidene protected disaccharide using dichlorophenylborane (PhBCl<sub>2</sub>) and triethylsilane (Et<sub>3</sub>SiH) to access a CS−D precursor, in 73 % yield over two steps. Finally, synthesis of a 6‐<em>O</em>‐sulfated CS−C disaccharide containing a conjugable anomeric allyl tether is completed. These materials will provide a benchmark to further synthesise and study chondroitin sulfates.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 40","pages":"Article e202400587"},"PeriodicalIF":2.5,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400587","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141794853","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Copper-Catalyzed Chemoselective Synthesis of Pyrazolo-Sulfonamide: Impact of Solvent on Nitro-pyrazole Reactivity 铜催化的吡唑磺酰胺化学选择性合成：溶剂对硝基吡唑反应活性的影响
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202401097
Subhendu Bhowmik, RANA SAHA, Swarnendu Dutta, Arka Das, Rajarshi Jana, Krutika Sonar, Sreya Gupta
{"title":"Copper-Catalyzed Chemoselective Synthesis of Pyrazolo-Sulfonamide: Impact of Solvent on Nitro-pyrazole Reactivity","authors":"Subhendu Bhowmik, RANA SAHA, Swarnendu Dutta, Arka Das, Rajarshi Jana, Krutika Sonar, Sreya Gupta","doi":"10.1002/ejoc.202401097","DOIUrl":"https://doi.org/10.1002/ejoc.202401097","url":null,"abstract":"Abstract: This study presents a copper-catalyzed, solvent-dependent method for the rapid and efficient synthesis of N-pyrazolo-sulfonamides directly from nitro-pyrazole and sulfonyl hydrazide under microwave conditions. The reaction exhibits notable solvent effects in pyrazole’s reactivity. The ionic liquid DBU-AcOH triggered the reactivity of 4-nitro-pyrazole, whereas the reaction in PEG proceeded selectively at the 3- &amp; 5-positions of pyrazole. Key applications of this method include the gram-scale synthesis of pyrazolo-sulfonamide, sulfaphenazole analogue and sulfonamide","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452371","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Perylene Based Twisted Emissive Curved Nanographene Synthesis through Scholl Reaction 通过烁尔反应合成基于苝的扭转发射型弯曲纳米石墨烯
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202401170
Siddhartha Samanta, Sahina Khatun, Sanhita Maity, Anirban Pradhan
{"title":"Perylene Based Twisted Emissive Curved Nanographene Synthesis through Scholl Reaction","authors":"Siddhartha Samanta, Sahina Khatun, Sanhita Maity, Anirban Pradhan","doi":"10.1002/ejoc.202401170","DOIUrl":"https://doi.org/10.1002/ejoc.202401170","url":null,"abstract":"A twisted chiral nanographene (NG) surrounded by eight bulky tert-butyl groups fused with emissive chromophore perylene was synthesized by highly regioselective cyclodehydrogenation strategy in which a double [6]helicene was formed simultaneously. The twisted 4-meso was unambiguously confirmed by single crystal X-ray analysis. The NG showed an excellent photoluminescence quantum yield (φf) of 55%, indicating its great potential for chiral optoelectronics.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142452374","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids 在合成氨基糖和多羟基联哌啶酸过程中稳定的 D-葡萄糖二硝酸盐
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-10-21 DOI: 10.1002/ejoc.202400395
Rosalino Balo, Andrés Fernández, David Reza, Pablo López, George W. J. Fleet, Ramón J. Estévez, Juan C. Estévez
{"title":"Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids","authors":"Rosalino Balo,&nbsp;Andrés Fernández,&nbsp;David Reza,&nbsp;Pablo López,&nbsp;George W. J. Fleet,&nbsp;Ramón J. Estévez,&nbsp;Juan C. Estévez","doi":"10.1002/ejoc.202400395","DOIUrl":"10.1002/ejoc.202400395","url":null,"abstract":"<p>A synthesis of the five membered iminosugar DAB and a divergent synthesis of the six membered iminosugar 1-dehydromannojirimycin (DMJ) and the corresponding sugar imino acid are reported. They involve double nucleophilic displacements of a D-xylose ditriflate by benzyl carbazate and a D-glucose ditriflate by allyl amine, respectively. They are followed by a similar protocol consisting of hydrolysis and oxidation or reduction of the resulting bicyclic glycosides. This allowed DMJ to be obtained from the cheap sugar D-glucose.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 42","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400395","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142486434","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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