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A Domino One-Pot Approach to Functionalized Benzonitriles from 2-[(3-Hydroxy/acetoxy)propyn-1-yl]benzamides 从 2-[(3-羟基/乙酰氧基)丙炔-1-基]苯甲酰胺制备功能化苯腈的多米诺一锅法
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/a-2356-8297
Sindoori R. Nair, Bhavani Shankar Chinta, Beeraiah Baire
{"title":"A Domino One-Pot Approach to Functionalized Benzonitriles from 2-[(3-Hydroxy/acetoxy)propyn-1-yl]benzamides","authors":"Sindoori R. Nair, Bhavani Shankar Chinta, Beeraiah Baire","doi":"10.1055/a-2356-8297","DOIUrl":"https://doi.org/10.1055/a-2356-8297","url":null,"abstract":"<p>Functionalized benzonitriles, α,β-epoxyketones and β-hydroxy-α-haloketones are found in numerous medicinally important molecules, whilst benzonitriles in combination with any of these functional groups may be of interest to medicinal chemists. However, the simultaneous incorporation of a nitrile group and these functional groups on the aromatic ring is a challenging task. Herein, we report a strategy for the rapid and simultaneous construction of structurally novel benzonitrile derivatives, possessing either an <i>ortho</i>-α-iodo-β-hydroxyketone, an α,β-epoxyketone or an α,β-enone, from unprotected, 2-[(3-hydroxy/acetoxy)propyn-1-yl]benzamides. This process involves NXS-promoted dehydration–halohydration followed by DIPEA-mediated epoxide formation (from alcohols). We have developed both stepwise and one-pot strategies to improve the synthetic efficiency. No metal catalyst is employed and the method exhibits good substrate scope and yields. </p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"91 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141718888","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2024/8 同步信息》第 2024/8 期
Synthesis Pub Date : 2024-07-15 DOI: 10.1055/s-0043-1763992
M. Zanda
{"title":"SYNFORM ISSUE 2024/8","authors":"M. Zanda","doi":"10.1055/s-0043-1763992","DOIUrl":"https://doi.org/10.1055/s-0043-1763992","url":null,"abstract":"","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"20 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141648338","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Annulation Reactions of Isoquinolinium Ylides with Sulfamate-Derived Cyclic Imines toward Polycyclic 1,3-Benzoxazepine Heterocycles 异喹啉鎓酰化物与氨基磺酸盐衍生环胺对多环 1,3-苯并氧氮杂环的环化反应
Synthesis Pub Date : 2024-07-11 DOI: 10.1055/a-2349-6944
Koushik Patra, Sana Mulani, Mahiuddin Baidya
{"title":"Annulation Reactions of Isoquinolinium Ylides with Sulfamate-Derived Cyclic Imines toward Polycyclic 1,3-Benzoxazepine Heterocycles","authors":"Koushik Patra, Sana Mulani, Mahiuddin Baidya","doi":"10.1055/a-2349-6944","DOIUrl":"https://doi.org/10.1055/a-2349-6944","url":null,"abstract":"<p>A dearomatization-guided and (3+2) cycloaddition-triggered annulation reaction of in situ formed isoquinolinium ylides with sulfamate-derived cyclic imines is reported, offering a cogent synthesis of tetracyclic 1,3-benzoxazepine frameworks in high yields. The protocol features successive ring-forming and ring-breaking events in a cascade fashion and is also scalable.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"71 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141612724","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Oxidative Cross-Dehydrogenative C–H Bond Amination of Imidazo[1,2-a]pyridines in Aqueous Media under Metal-Free Conditions 无金属条件下水介质中咪唑并[1,2-a]吡啶的交叉脱氢 C-H 键氧化胺化反应
Synthesis Pub Date : 2024-07-10 DOI: 10.1055/a-2348-4764
Durgesh Sarothiya, Umesh A. Kshirsagar
{"title":"Oxidative Cross-Dehydrogenative C–H Bond Amination of Imidazo[1,2-a]pyridines in Aqueous Media under Metal-Free Conditions","authors":"Durgesh Sarothiya, Umesh A. Kshirsagar","doi":"10.1055/a-2348-4764","DOIUrl":"https://doi.org/10.1055/a-2348-4764","url":null,"abstract":"<p>The metal-free direct oxidative cross-dehydrogenative C–H bond amination of imidazopyridines with pyrazole in water as solvent has been developed under K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-promoted mild conditions. This strategy was applied to variable imidazoheterocycles to give amination products in moderate to good yields. The described protocol also offers scale-up synthesis for the construction of C–N bonds, which makes it suitable for the synthesis of biologically active compounds and pharmaceuticals.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"53 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141585140","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Spirocyclic Hybrids of Nortropane and 1,3-Oxazinan-2-one Fragments 正托烷和 1,3-恶嗪酮-2-酮片段的螺环杂化物
Synthesis Pub Date : 2024-07-08 DOI: 10.1055/a-2335-4444
Alexandr Mandzhulo, Iryna Vashchenko, Oleg Lukin, Svetlana Shishkina, Grygoriy Dolgonos, Andrii Gerasov, Vitaliy Yepishev, Dariia Samofalova, Volodymyr Fetyukhin, Alexander Shivanyuk
{"title":"Spirocyclic Hybrids of Nortropane and 1,3-Oxazinan-2-one Fragments","authors":"Alexandr Mandzhulo, Iryna Vashchenko, Oleg Lukin, Svetlana Shishkina, Grygoriy Dolgonos, Andrii Gerasov, Vitaliy Yepishev, Dariia Samofalova, Volodymyr Fetyukhin, Alexander Shivanyuk","doi":"10.1055/a-2335-4444","DOIUrl":"https://doi.org/10.1055/a-2335-4444","url":null,"abstract":"<p>We report facile and versatile procedures for the synthesis of <i>exo</i>- and <i>endo</i>-isomeric spirocyclic hybrids of pharmacophoric (1<i>R</i>,5<i>S</i>)-8-azabicyclo[3.2.1]octane (nortropane) and 1,3-oxazinan-2-one fragments. Our approach consists of the hydrocyanation of <i>endo</i>- and <i>exo</i>-isomeric <i>N</i>-Cbz-protected nortropane-3-spiroepoxides, the reduction of hydroxy nitriles into amino alcohols, the synthesis of <i>N</i>-alkylated amino alcohols <i>via</i> reductive amination, the spirocyclization of the amino alcohols, <i>N</i>-alkylation of the unsubstituted 1,3-oxazinan-2-one fragment in the spiro compounds, and removal of the Cbz protecting groups.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"17 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141574916","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Asymmetric Organocatalytic Benzylation of Morita−Baylis−Hillman Carbonates with 2,4-Dinitrotoluene Derivatives 莫里塔-贝利斯-希尔曼碳酸盐与 2,4-二硝基甲苯衍生物的不对称有机催化苄化反应
Synthesis Pub Date : 2024-07-05 DOI: 10.1055/a-2361-0011
Yu-Da Wu, Bo Huang, Yu-Chun Chen, Jeng‐Liang Han
{"title":"Asymmetric Organocatalytic Benzylation of Morita−Baylis−Hillman Carbonates with 2,4-Dinitrotoluene Derivatives","authors":"Yu-Da Wu, Bo Huang, Yu-Chun Chen, Jeng‐Liang Han","doi":"10.1055/a-2361-0011","DOIUrl":"https://doi.org/10.1055/a-2361-0011","url":null,"abstract":"We here described the organocatalytic asymmetric benzylation of Morita−Baylis−Hillman (MBH) carbonates with 2,4-dinitrotoluene derivatives as nucleophiles. The developed reaction provides a straightforward access to functionalized 2,4-dinitrotoluene derivatives of biological and synthetic relevance. Highly functionalized products have been chemoselectively and efficiently obtained in good to high yield (up to 84%) and with excellent stereoselectivity (up to >20:1 dr, >99 ee).","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":" 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141676584","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Efficient Oxidation with Singlet Oxygen from 5,10,15,20-Tetraphenylporphyrin under Blue LED Irradiation and Air Atmosphere: Simplified Preparation of Key Building Blocks for Natural Product Synthesis 在蓝光 LED 照射和空气环境下，5,10,15,20-四苯基卟啉与单线态氧的高效氧化：简化天然产物合成关键组分的制备过程
Synthesis Pub Date : 2024-07-05 DOI: 10.1055/a-2361-0069
Masato Hasumi, Tomohiro Tsutsumi, Daiki Shikama, Ichiro Hayakawa
{"title":"Efficient Oxidation with Singlet Oxygen from 5,10,15,20-Tetraphenylporphyrin under Blue LED Irradiation and Air Atmosphere: Simplified Preparation of Key Building Blocks for Natural Product Synthesis","authors":"Masato Hasumi, Tomohiro Tsutsumi, Daiki Shikama, Ichiro Hayakawa","doi":"10.1055/a-2361-0069","DOIUrl":"https://doi.org/10.1055/a-2361-0069","url":null,"abstract":"A method for preparing important building blocks for natural product synthesis has been developed using singlet oxygen generated from 5,10,15,20-tetraphenylporphyrin (TPP) under blue LED irradiation. Using this method, the allylic oxidation of dicyclopentadiene proceeded smoothly in air atmosphere with an 87% yield. This condition, using TPP under blue LED irradiation, was expanded to include the oxidation of cyclopentadiene. It is a simple and cost-effective method of synthesizing important building blocks for natural product synthesis.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":" 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141674321","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 Domino Heteroarylation of Thioamides: A Simple Route to Benzothieno[2,3-b]quinolones 钯催化的多米诺硫酰胺异芳基化反应：获得苯并噻吩并[2,3-b]喹啉酮的简单途径
Synthesis Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8167
M. Janni, Annaram Thirupathi, Subhashini V Subramanian, S. Peruncheralathan
{"title":"Palladium-Catalyzed Domino Heteroarylation of Thioamides: A Simple Route to Benzothieno[2,3-b]quinolones","authors":"M. Janni, Annaram Thirupathi, Subhashini V Subramanian, S. Peruncheralathan","doi":"10.1055/a-2360-8167","DOIUrl":"https://doi.org/10.1055/a-2360-8167","url":null,"abstract":"Domino reactions are essential for advancing organic synthesis. This study introduces novel thioamide-based precursors for a palladium-catalyzed selective domino heteroarylation process. The method efficiently produces benzothieno[2,3-b]quinolones with yields ranging from moderate to very good. By employing aryl chlorides, the efficiency of the domino heteroannulation process is comparable to that of aryl bromides. Executing a one-pot, two-step reaction also delivered a single domino product with high selectivity. The strategy involved fine-tuning substituent reactivity, utilizing electron-rich arenes, and forming metallocycles with nucleophilic sulfur, consistently yielding a single product. The proposed mechanism is corroborated by mechanistic studies.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":" 14","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141679803","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 Heterocycles by HNTf2-Catalyzed C−H Functionalization of Vinyldiazo Compounds with 3-Hydroxyisoindolinone 通过 HNTf2 催化乙烯基重氮化合物与 3-羟基异吲哚啉酮的 C-H 功能化合成杂环化合物
Synthesis Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8359
Michael P. Doyle, Ming Bao, Hadi D Arman
{"title":"Synthesis of Heterocycles by HNTf2-Catalyzed C−H Functionalization of Vinyldiazo Compounds with 3-Hydroxyisoindolinone","authors":"Michael P. Doyle, Ming Bao, Hadi D Arman","doi":"10.1055/a-2360-8359","DOIUrl":"https://doi.org/10.1055/a-2360-8359","url":null,"abstract":"A Brønsted acid catalyzed C−H functionalization of vinyldiazoacetates with 3-hydroxyisoindolinone has been developed. This methodology provides a general access to E-substituted isoindolinone vinyldiazo compounds in good yields and excellent diastereoseletivity with broad substrate generality under mild conditions, and with 4-substituted-2-diazo-3-butenoates produces fused bicyclic pyrrolidines. The reaction generally involves addition of the N-acyl ketiminium electrophile formed from the 3-hydroxyisoindolinone to the vinylogous position of vinyldiazo compounds that results in vinyldiazonium ion intermediates that undergo deprotonation to new vinyldiazo compounds or ring closure to fused bicyclic pyrrolidines.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":" 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141678813","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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 Asymmetric Trifluoromethylated Allylic Alkylation of Azlactone: Efficient Access to Unsaturated α-Quaternary Stereogenic α-Amino Acid Derivatives 钯催化的氮内酯不对称三氟甲基化烯丙基烷基化反应：高效获取不饱和 α-季立体源性 α-氨基酸衍生物
Synthesis Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8289
Shuaibo Zhang, Lu Sun, Dong Li, Jinfeng Zhao, Jingping Qu, Yuhan Zhou
{"title":"Palladium-catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of Azlactone: Efficient Access to Unsaturated α-Quaternary Stereogenic α-Amino Acid Derivatives","authors":"Shuaibo Zhang, Lu Sun, Dong Li, Jinfeng Zhao, Jingping Qu, Yuhan Zhou","doi":"10.1055/a-2360-8289","DOIUrl":"https://doi.org/10.1055/a-2360-8289","url":null,"abstract":"An unprecedented strategy for asymmetric trifluoromethylated allylic alkylation of azlactone with α-(trifluoromethyl)allyl acetate catalyzed by a Pd(OAc)2/(R)-BINAP has been rationally designed and developed, providing various unsaturated α-quaternary α-amino acid derivatives bearing trifluoromethyl groups, contigous quaternary and tertiary stereogenic centers in good yields with exclusive regioselectivity and excellent stereoselective control under relatively mild reaction conditions. The scale-up experiment has shown no loss of reactivity and stereoselectivity, the synthetic utility of the current strategy is testified through product transformations to obtain some important bioactivity species.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":" 8","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141678829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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