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Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst 清洁反应条件下的无受体脱氢反应：以支撑镍氮氧化物为催化剂合成 2-芳基/烷基喹唑啉酮
IF 2 4区 化学
Synlett Pub Date : 2024-09-18 DOI: 10.1055/a-2388-9487
Vageesh MM, Omkar Patil, Hima PP, Raju Dey
{"title":"Acceptorless Dehydrogenation under Neat Reaction Conditions: Synthesis of 2-Aryl/Alkyl Quinazolinones Using Supported Ni NPs as Catalyst","authors":"Vageesh MM, Omkar Patil, Hima PP, Raju Dey","doi":"10.1055/a-2388-9487","DOIUrl":"https://doi.org/10.1055/a-2388-9487","url":null,"abstract":"<p>We report here a Ni-NPs-catalyzed one-pot synthesis of 2-alkyl/aryl quinazolinone motifs <i>via</i> acceptorless dehydrogenation of alcohol, condensation of an aldehyde intermediate with 2-aminobenzamide, followed by a second dehydrogenation of the cyclized intermediate. The protocol is atom-economical and require earth-abundant Ni as the catalyst. The present report involves the annulation of 2-aminobenzamide with various types of primary alcohols, including aryl/heteroaryl methanol, and aliphatic alcohols, and produces high yields of the desired products under neat conditions. The catalyst was synthesized <i>via</i> a high-temperature pyrolysis strategy, using ZIF-8 as the sacrificial template. The Ni NPs@N-C catalyst was characterized by XPS, HR-TEM, HAADF-STEM, XRD, and ICP-MS. The catalyst is stable even in air at room temperature and displayed excellent activity in the acceptorless dehydrogenative coupling synthesis of quinazolinones and could be recycled five times without appreciable loss of its activity.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"29 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261305","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
Comparison of the Effects of Stirring and Standing on Chemical Reactions 搅拌和静置对化学反应影响的比较
IF 2 4区 化学
Synlett Pub Date : 2024-09-18 DOI: 10.1055/a-2384-7220
Xianting Huang, Jianyou Zhao, Qingxu Wang, Pengkai Fang, Wei Xie, Meng Chen, Hongliang Han, Lanlan Zhang, Jiatai Zhang, Fan Wang, Zhong-Quan Liu
{"title":"Comparison of the Effects of Stirring and Standing on Chemical Reactions","authors":"Xianting Huang, Jianyou Zhao, Qingxu Wang, Pengkai Fang, Wei Xie, Meng Chen, Hongliang Han, Lanlan Zhang, Jiatai Zhang, Fan Wang, Zhong-Quan Liu","doi":"10.1055/a-2384-7220","DOIUrl":"https://doi.org/10.1055/a-2384-7220","url":null,"abstract":"<p>For hundreds of years, it seems that people have needed stirring to conduct chemical experiments. This operation can be seen everywhere in chemical, pharmaceutical, and materials laboratories and factories. People generally believe that stirring helps with processes such as material dispersion, dissolution, and collision, thereby enabling more-efficient reactions. However, why do chemical reactions that occur in Nature not require stirring? What are the facts? For this purpose, we investigated a total of 329 organic chemical reactions in eight categories and 25 types, including 26 chemical reactions magnified to gram or even kilogram levels. Under the same conditions of temperature, humidity, pressure, and reaction time, we compared the reaction yields under stirring and standing conditions. More than 600 results showed that stirring or not stirring had almost no effect on the efficiency of chemical reactions in solution. If most chemists performing reactions turned off the agitator, it would not be difficult to imagine how much electricity could be saved!</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"41 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261306","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
Sustainable N-Formylation of Anilines: Harnessing Aleuritic Acid as a Renewable Formyl Source 苯胺的可持续 N-甲酰化：利用阿留申酸作为可再生甲酰基来源
IF 2 4区 化学
Synlett Pub Date : 2024-09-18 DOI: 10.1055/a-2388-9578
Hetavi A. Vadariya, Gaurav Badhani, B. Mohamed Farves, Krupa N. Boda, Subbarayappa Adimurthy
{"title":"Sustainable N-Formylation of Anilines: Harnessing Aleuritic Acid as a Renewable Formyl Source","authors":"Hetavi A. Vadariya, Gaurav Badhani, B. Mohamed Farves, Krupa N. Boda, Subbarayappa Adimurthy","doi":"10.1055/a-2388-9578","DOIUrl":"https://doi.org/10.1055/a-2388-9578","url":null,"abstract":"<p>\u0000<i>N</i>-Formylation of anilines using a renewable aleuritic acid as an eco-friendly and sustainable formylating source has been developed. <i>para</i>-Substituted anilines generally provided good yields, while moderate yields were observed with <i>meta</i>- and <i>ortho</i>-substituted derivatives. <i>In situ</i> generated formic acid through oxidative cleavage of aleuritic acid serve as a formyl source, which has been confirmed through control experiments.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"195 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261304","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
Nickel-Catalyzed O-Methylation of Cinnamic Acid Using DMSO as Methyl Surrogate 镍催化肉桂酸的 O-甲基化反应（使用二甲基亚砜作为甲基替代物
IF 2 4区 化学
Synlett Pub Date : 2024-09-16 DOI: 10.1055/a-2384-6807
Hrishikesh Talukdar, Prodeep Phukan
{"title":"Nickel-Catalyzed O-Methylation of Cinnamic Acid Using DMSO as Methyl Surrogate","authors":"Hrishikesh Talukdar, Prodeep Phukan","doi":"10.1055/a-2384-6807","DOIUrl":"https://doi.org/10.1055/a-2384-6807","url":null,"abstract":"<p>A new method for the <i>O</i>-methylation of cinnamic acid employing DMSO as the methylating agent has been devised, employing a Ni-DMAP complex as catalyst along with Ag<sub>2</sub>O and dimethylamine as additives. This protocol demonstrates broad substrate compatibility and good tolerance towards various functional groups. The key advantages of this approach include the utilization of cost-effective catalysts, moderate to high yield of the products, and short reaction time.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"26 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142261307","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
Skeletal Reorganization: Approaches towards the Synthesis of Aza-Heterocyclic Cores 骨架重组：合成氮杂环核心的方法
IF 2 4区 化学
Synlett Pub Date : 2024-09-12 DOI: 10.1055/a-2384-6583
Dwaipayan Das, Rahul Dev Mandal, Prasun Mukherjee, Pranabes Bhattacharya, Asish R. Das
{"title":"Skeletal Reorganization: Approaches towards the Synthesis of Aza-Heterocyclic Cores","authors":"Dwaipayan Das, Rahul Dev Mandal, Prasun Mukherjee, Pranabes Bhattacharya, Asish R. Das","doi":"10.1055/a-2384-6583","DOIUrl":"https://doi.org/10.1055/a-2384-6583","url":null,"abstract":"<p>The impetuous development of the pharmaceutical industry and material science stimulates the search for new synthetic approaches and new methods for the synthesis and functionalization of aza-heterocycles; these are some of the key objectives of modern organic chemistry. As a result, an advanced method towards the synthesis of functionalized N-heterocycles that circumvents the limitations associated with traditional methods needs to be devised. In recent decades, rearrangement/reorganization reactions have emerged as a powerful tool for the efficient synthesis of the aza-heterocycle. In this illustration, we summarize some our recent efforts in the development of few complex aza-heterocyclic cores.</p> <p>1 Introduction</p> <p>2 Skeletal Rearrangement of Small Heterocycles via Domino Ring-Opening and Ring-Closing (DROC) Strategy</p> <p>3 Ru(II)-Catalyzed Skeletal Rearrangement of the Quinazoline Ring</p> <p>4 Lewis Acid Catalyzed Skeletal Rearrangement of Furans to Indolizine Cores</p> <p>5 Skeletal Rearrangement of Donor–Acceptor Cyclopropanes via Domino Ring-Opening and Ring-Closing (DROC) Strategy</p> <p>6 Lewis Acid Mediated Skeletal Rearrangement of Donor–Acceptor Spirocyclopropylpyrazolones</p> <p>7 Skeletal Rearrangement through Ring Distortion Strategy</p> <p>8 Conclusion</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"58 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210257","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 Phosphorodiamidate Morpholino Oligonucleotides (PMOs) Using Staudinger Reduction as a Deblocking Condition and Its Usefulness for Orthogonal Conjugation in Bi- and Trifunctionalized PMOs 使用施陶丁格还原法作为解锁条件合成磷酸二酰胺吗啉寡核苷酸（PMOs）及其在双官能化和三官能化 PMOs 的正交共轭中的用途
IF 2 4区 化学
Synlett Pub Date : 2024-09-11 DOI: 10.1055/a-2384-7323
Subhamoy Pratihar, Md Qasim, Surajit Sinha
{"title":"Synthesis of Phosphorodiamidate Morpholino Oligonucleotides (PMOs) Using Staudinger Reduction as a Deblocking Condition and Its Usefulness for Orthogonal Conjugation in Bi- and Trifunctionalized PMOs","authors":"Subhamoy Pratihar, Md Qasim, Surajit Sinha","doi":"10.1055/a-2384-7323","DOIUrl":"https://doi.org/10.1055/a-2384-7323","url":null,"abstract":"<p>The synthesis of short phosphorodiamidate morpholino oligonucleotides (PMOs) has been successfully achieved using azidoaryl carbamate protected chlorophosphoramidate monomers. The deprotection step carried out in a neutral medium with triphenylphosphine-based reagents avoids the need for chlorinated solvents. This method uses a meticulously tailored combination of resin support, solvents, deblocking agents, and coupling reagents to ensure efficient synthesis. Additionally, the azidoaryl carbamate protecting group has been adapted as an orthogonal protection, enabling the development of bi- and trifunctionalized PMOs for bioconjugation. These advancements are expected to broaden the potential applications of PMOs in biomedical research.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"9 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210258","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
Design and Synthesis of Out/Out, Out/In, and In/In Epoxides in Polycyclic Cage Frameworks 多环笼框架中外/内、外/内和内/内环氧化物的设计与合成
IF 2 4区 化学
Synlett Pub Date : 2024-09-10 DOI: 10.1055/a-2384-6736
Sambasivarao Kotha, Mohammad Salman
{"title":"Design and Synthesis of Out/Out, Out/In, and In/In Epoxides in Polycyclic Cage Frameworks","authors":"Sambasivarao Kotha, Mohammad Salman","doi":"10.1055/a-2384-6736","DOIUrl":"https://doi.org/10.1055/a-2384-6736","url":null,"abstract":"<p>We report a useful synthetic approach to assemble in/in epoxide, in/out epoxide, and out/out epoxide in cage systems using the Corey–Chaykovsky reaction and the Peterson olefination as key steps. In this regard, a variety of pentacycloundecane (PCUD) based cage compounds containing oxirane rings with diverse stereochemical disposition were synthesized <i>via</i> a simple synthetic sequence. Five cage diones were used for this purpose, and the starting cage diones were prepared with easily accessible starting materials such as 1,4-hydroquinone derivatives and cyclopentadiene. Here, we have used the Diels–Alder (DA) reaction, a [2+2] photocycloaddition, the Corey–Chaykovsky reaction, and the Peterson olefination as crucial steps to prepare the target molecules.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"7 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226694","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
Sequential Copper-Catalyzed Amidation and Hydroxylation for Acetaminophen Synthesis 铜催化的乙酰氨基酚合成中的顺序酰胺化和羟基化反应
IF 2 4区 化学
Synlett Pub Date : 2024-09-10 DOI: 10.1055/a-2384-7081
Youngran Seo, Dongwon Yoo, Young Gyu Kim
{"title":"Sequential Copper-Catalyzed Amidation and Hydroxylation for Acetaminophen Synthesis","authors":"Youngran Seo, Dongwon Yoo, Young Gyu Kim","doi":"10.1055/a-2384-7081","DOIUrl":"https://doi.org/10.1055/a-2384-7081","url":null,"abstract":"<p>A sequential Cu-catalyzed amidation and hydroxylation of <i>p</i>-dihalobenzenes is applied to synthesize acetaminophen. This method allows the direct introduction of acetamido and hydroxy groups under acid-free conditions without forming other regioisomers. By using a one-pot process, acetaminophen can be prepared with an overall yield of up to 74%.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"24 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210259","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
Design of Molecular Diversity by Olefin Metathesis in Tandem with Other Reactions 通过烯烃官能团与其他反应设计分子多样性
IF 2 4区 化学
Synlett Pub Date : 2024-09-10 DOI: 10.1055/a-2379-9912
Sambasivarao Kotha, Naveen Kumar Gupta, Saima Ansari, Deepshikha Singh
{"title":"Design of Molecular Diversity by Olefin Metathesis in Tandem with Other Reactions","authors":"Sambasivarao Kotha, Naveen Kumar Gupta, Saima Ansari, Deepshikha Singh","doi":"10.1055/a-2379-9912","DOIUrl":"https://doi.org/10.1055/a-2379-9912","url":null,"abstract":"<p>This review summarizes various strategies that combine metathesis with diverse named and unnamed reactions to create molecular diversity in producing carbocycles, macrocycles, and heterocycles.</p> <p>1\tIntroduction</p> <p>2 Olefinations</p> <p>3 Rearrangement</p> <p>4 Allylation</p> <p>5 Cycloadditions</p> <p>6 Coupling Reactions</p> <p>7 Grignard Reaction</p> <p>8 Radical reactions</p> <p>9 Conjugate Addition–Metathesis</p> <p>10 Multicomponent Reactions</p> <p>11 Miscellaneous</p> <p>12 Conclusions</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"112 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226695","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
NiCo2O4-Nanoparticle-Catalyzed Microwave-Assisted Dehydrogenative Direct Oxidation of Primary Alcohols to Carboxylic Acids under Oxidant-Free Conditions 无氧化剂条件下镍钴氧化物-纳米粒子催化的微波辅助伯醇直接氧化成羧酸的脱氢反应
IF 2 4区 化学
Synlett Pub Date : 2024-09-09 DOI: 10.1055/a-2384-6371
Kumari Anchal, Ashok R. Patel, Subhash Banerjee
{"title":"NiCo2O4-Nanoparticle-Catalyzed Microwave-Assisted Dehydrogenative Direct Oxidation of Primary Alcohols to Carboxylic Acids under Oxidant-Free Conditions","authors":"Kumari Anchal, Ashok R. Patel, Subhash Banerjee","doi":"10.1055/a-2384-6371","DOIUrl":"https://doi.org/10.1055/a-2384-6371","url":null,"abstract":"<p>Here, we report the NiCo<sub>2</sub>O<sub>4</sub>-nanoparticle-catalyzed dehydrogenative direct oxidation of primary alcohols to carboxylic acid in the presence of KOH under microwave irradiation in the absence of any oxidant in good to excellent yields (75–99%) within a short reaction time (5–10 min). The polycrystalline cubic spinel phase of NiCo<sub>2</sub>O<sub>4</sub> nanoparticles (NPs) with an average size of 25 nm were synthesized by the co-precipitation method and analyzed properly by using powder X-ray diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, and transmission electron microscopy measurements. The NiCo<sub>2</sub>O<sub>4</sub> NPs were stable under the reaction conditions and reused for up to eight cycles without appreciable loss in the yield of benzoic acid. According to mechanistic insight, the KOH acts as a second oxygen source and is essential for the synthesis of carboxylic acid from alcohols. The hydrogen gas was found to be the only byproduct of this method detected by chemical reactions.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"8 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210261","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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