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A Formal [3+3] Annulation of Morita–Baylis–Hillman Ketones to Construct Pyrimidobenzothiazoles 莫里塔-贝利斯-希尔曼酮的正式[3+3]嵌合构建嘧啶并噻唑
Synthesis Pub Date : 2024-07-25 DOI: 10.1055/a-2373-0255
Rajkiran Kumari, Suman Kumawat, Easwar Srinivasan
{"title":"A Formal [3+3] Annulation of Morita–Baylis–Hillman Ketones to Construct Pyrimidobenzothiazoles","authors":"Rajkiran Kumari, Suman Kumawat, Easwar Srinivasan","doi":"10.1055/a-2373-0255","DOIUrl":"https://doi.org/10.1055/a-2373-0255","url":null,"abstract":"A calcium triflate promoted reaction of Morita–Baylis–Hillman (MBH) ketones, derived by the oxidation of MBH adducts, with 2-aminobenzothiazoles resulted in the formation of a 4H-pyrimido[2,1-b]benzothiazole. Formally, the transformation represents a [3+3] annulation and presumably proceeds via an aza-Michael addition followed by an intramolecular condensation. The reaction is completely regioselective and tolerates a wide range of substrates to afford a variety of analogs of the fused heterocycle in good yields.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"77 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141802273","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
Hypervalent Iodine-Mediated Ring-Opening 1,3-Difluorination of Benzylidenecyclopropanes 高价碘介导的亚苄基环丙烷开环 1,3-二氟化反应
Synthesis Pub Date : 2024-07-25 DOI: 10.1055/a-2373-0304
Long-Ling Huang, Jia-Yi Li, Qigang Sun, Gui-Yang Zhao, Honggen Wang, Qingjiang Li
{"title":"Hypervalent Iodine-Mediated Ring-Opening 1,3-Difluorination of Benzylidenecyclopropanes","authors":"Long-Ling Huang, Jia-Yi Li, Qigang Sun, Gui-Yang Zhao, Honggen Wang, Qingjiang Li","doi":"10.1055/a-2373-0304","DOIUrl":"https://doi.org/10.1055/a-2373-0304","url":null,"abstract":"1,3-Difluorinated compounds are characterized by their unique conformation, influenced by 1,3-dipolar minimization effects. However, their synthetic methods are relatively limited. Here, we describe a ring-opening 1,3-difluorination of benzylidenecyclopropanes (BCPs) using HF·Py, mediated by an electron-poor hypervalent iodine reagent, which is generated in-situ by the oxidation of o-nitroiodobenzene with mCPBA. The protocol features mild reaction conditions, good functional group tolerance, and moderate to good yields. Additionally, the synthetic utility of this method is showcased by further transformations of the olefin group and allylic fluoride motif.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"51 42","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141805045","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
One-Pot, Two-Step Synthesis of Highly Functionalized 4-Indolyl/Pyrrolyl-Chromanes via para-Quinone Methide Formation-1,8-Addition Sequence 通过对位醌甲酰胺形成-1,8-加成序列一步法合成高官能度 4-吲哚基/吡咯烷基色曼烷
Synthesis Pub Date : 2024-07-23 DOI: 10.1055/a-2371-3579
Rafia Khatoon, Tanvi Jandial, Anish Gupta, Sujata Kundan, V. Sridharan
{"title":"One-Pot, Two-Step Synthesis of Highly Functionalized 4-Indolyl/Pyrrolyl-Chromanes via para-Quinone Methide Formation-1,8-Addition Sequence","authors":"Rafia Khatoon, Tanvi Jandial, Anish Gupta, Sujata Kundan, V. Sridharan","doi":"10.1055/a-2371-3579","DOIUrl":"https://doi.org/10.1055/a-2371-3579","url":null,"abstract":"An efficient one-pot, two-step synthesis of structurally diverse 4-indolyl/pyrrolyl-chromanes was developed starting from O-propargylated salicylaldehydes, 2,6-dialkylphenols and indoles/pyrrole. This process begins with a sequential secondary amine-catalyzed formation of p-quinone methides followed by Brønsted acid-catalyzed 1,8-addition with indoles/pyrrole to access the functionalized chromanes in high yields (up to 91%). This sequential reaction generates three new C–C bonds, shows high step- and atom-economy with only one molecule of water as the side product and gives access to complex molecular frameworks without the need for the isolation of the intermediates.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"89 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141812734","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 Difluoromethyl Chromono[3,2-c]pyrazolines/pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with 3-EWG-Chromones 二氟乙酰丙酮溴化物与 3-EWG-Chromones 的 [3+2] 环加成反应合成二氟甲基色并[3,2-c]吡唑/吡唑
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2368-8392
Ke‐Hu Wang, Xiuwen Liang, Wenjing Luo, Maizhuo Chen, Junjiao Wang, Danfeng Huang, Yulai Hu
{"title":"Synthesis of Difluoromethyl Chromono[3,2-c]pyrazolines/pyrazoles by [3+2] Cycloaddition Reaction of Difluoroacetohydrazonoyl Bromides with 3-EWG-Chromones","authors":"Ke‐Hu Wang, Xiuwen Liang, Wenjing Luo, Maizhuo Chen, Junjiao Wang, Danfeng Huang, Yulai Hu","doi":"10.1055/a-2368-8392","DOIUrl":"https://doi.org/10.1055/a-2368-8392","url":null,"abstract":"A highly convenient and straightforward strategy for the synthesis of difluoromethyl substituted tricyclic fused chromono[3,2-c]pyrazolines/pyrazoles is developed via [3+2]-cycloaddition of difluoroacetohydrazonoyl bromides with 3-electron-withdrawing-group substituted chromones. The reaction has the advantages of mild conditions, good tolerance of functional groups and simple operation.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 71","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141825203","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
Chemical Methods for Construction of Spirocyclic β-Lactams and their Biological Importance 构建螺环β-内酰胺的化学方法及其生物学意义
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2368-8443
Pooja Yadav, Shiwani Berry, Aman Bhalla
{"title":"Chemical Methods for Construction of Spirocyclic β-Lactams and their Biological Importance","authors":"Pooja Yadav, Shiwani Berry, Aman Bhalla","doi":"10.1055/a-2368-8443","DOIUrl":"https://doi.org/10.1055/a-2368-8443","url":null,"abstract":"Spirocyclic β-lactams are a family of natural and synthetic chemicals with different biological activity, including antibacterial properties and interaction with critical physiological targets such as T-type calcium channels and acetyl-CoA cholesterol acyltransferase. Their unique chemical structure, combining spiro ring system with β-lactam group, offers promising opportunities for targeted medication discovery in medicinal chemistry. Spirocyclic β-lactams have the potential to be adaptable frameworks for developing novel therapeutic medicines with particular three-dimensional pharmacophoric characteristics and increased biological efficacy. Numerous methods are employed in the synthesis of spirocyclic β-lactams, such as cyclization, functional group modifications, asymmetric synthesis utilizing chiral catalysts and biomimetic approaches. In this Short Review, two distinct approaches to recent synthesis of spirocyclic β-lactams are discussed: one is based on constructing the β-lactam ring, while the other entails transforming monocyclic β-lactams into spirocyclic structures (from 2021 to till date). These methods include detailed reaction processes and biological function descriptions of target spirocycles. The applications of spirocyclic β-lactams in medicinal chemistry highlight their role in synthesis of structurally diverse compounds with significant therapeutic potential, demonstrating creative chemical methods of building complex molecular structures. \u00001 Introduction \u00002 β-Lactam Ring Synthesis \u00003 Non-β-Lactam Ring Synthesis \u00004 Miscellaneous Examples \u00005 Conclusion and Outlook \u00006 References","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 24","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141825998","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
Mild and stereoselective synthesis of (1E,3E)-dienes through silver(I)-catalyzed β-hydride migration from allylic α-diazo esters 通过银(I)催化的烯丙基α-重氮酯β-酸酐迁移，温和、立体选择性地合成(1E,3E)-二烯
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2369-3961
Marcus M. Sá, P. A. Moro, Theo V. C. Russo, Vinicius C Port, G. Caramori
{"title":"Mild and stereoselective synthesis of (1E,3E)-dienes through silver(I)-catalyzed β-hydride migration from allylic α-diazo esters","authors":"Marcus M. Sá, P. A. Moro, Theo V. C. Russo, Vinicius C Port, G. Caramori","doi":"10.1055/a-2369-3961","DOIUrl":"https://doi.org/10.1055/a-2369-3961","url":null,"abstract":"A mild procedure for the diastereoselective preparation of functionalized 1,3-dienes and their synthetic versatility are described herein. The silver-catalyzed decomposition of α-diazo-γ,δ-unsaturated esters through β-hydride migration at room temperature resulted in the stereoselective formation of 12 conjugated (1E,3E)-dienes. Further synthetic post-modifications included intramolecular Heck reaction and hydrogenation, leading to a novel substituted indene and an aliphatic diester, respectively. To rationalize the observed reaction outcome, a computational investigation of the mechanisms was conducted, emphasizing the importance of factors such as metallocarbenoid stability, substituent effects, and microkinetics simulations to better understand the reaction intricacies.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141824403","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
Catalytic asymmetric synthesis of 3-monosubstituted oxindoles 3- 单取代吲哚的催化不对称合成
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2368-8554
Xigong Liu, Lei Liu
{"title":"Catalytic asymmetric synthesis of 3-monosubstituted oxindoles","authors":"Xigong Liu, Lei Liu","doi":"10.1055/a-2368-8554","DOIUrl":"https://doi.org/10.1055/a-2368-8554","url":null,"abstract":"Chiral 3-monosubstituted oxindoles are privileged structural motifs in a variety of natural products and synthetic pharmaceuticals. However, catalytic asymmetric synthesis of these structural motifs has remained a challenge mainly because of the ease of racemization of the tertiary stereocenter through enolization. In this short review, asymmetric synthetic methods for chiral 3-monosubstituted oxindoles are summarized from the perspective of four different strategies, including Michael addition, carbenoid-mediated C‒H insertion, decarboxylative protonation, and indole oxidation.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 14","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141827206","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
Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones 过渡金属催化的咪唑并[2,1-b]噻唑的快速合成：通过 2-氨基噻唑和苯乙酮的有氧氧化偶联获得氮杂融合杂环
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2369-3893
Soumyadipta Basak, Pratap Paul, J. Dash
{"title":"Transition-Metal Catalyzed Rapid Synthesis of Imidiazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones","authors":"Soumyadipta Basak, Pratap Paul, J. Dash","doi":"10.1055/a-2369-3893","DOIUrl":"https://doi.org/10.1055/a-2369-3893","url":null,"abstract":"We report an efficient synthesis of 6-substituted imidazo[2,1-b]thiazoles through intramolecular cyclization of in situ generated thiazolium ylide from 2-aminothiazole and acetophenone. This one-pot cascade process efficiently forms two C-N bonds and is facilitated by Cu(OTf)2 and KI, both of which play key roles in the mechanism. The method utilizes commercially available starting materials and features mild reaction conditions, tolerance to different functional groups, and ease of operation. The synthetic applicability has further been demonstrated through post-modification of imidazo[2,1-b]thiazole analogues.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 36","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141827838","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
Lewis acid mediated synthesis of 4-aminoquinoline derivatives from 2-aminobenzonitriles and activated alkynes via aza-Michael and annulation reaction 以路易斯酸为介质，通过氮杂迈克尔反应和环化反应，从 2-氨基苯腈和活化炔合成 4-氨基喹啉衍生物
Synthesis Pub Date : 2024-07-18 DOI: 10.1055/a-2368-8500
A. Saikia, Bikoshita Porashar
{"title":"Lewis acid mediated synthesis of 4-aminoquinoline derivatives from 2-aminobenzonitriles and activated alkynes via aza-Michael and annulation reaction","authors":"A. Saikia, Bikoshita Porashar","doi":"10.1055/a-2368-8500","DOIUrl":"https://doi.org/10.1055/a-2368-8500","url":null,"abstract":"An efficient methodology for the synthesis of highly diverse 4-aminoquinoline derivatives from activated alkynes and 2-aminobenzonitriles mediated by Lewis acid is described. The reaction proceeds via sequential aza-Michael addition/intramolecular annulation to afford highly substituted 4-aminoquinolines in good yields. The reaction is operationally simple and has high atom-economy with broad substrate scope. The post synthetic application of the reaction provides 4H-benzo[de][1,6]naphthyridines.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":" 36","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141824593","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
Redox-Neutral 1,2-Dicarbonfunctionlization of 1,3-Butadiene by Merging Decatungstate and Chromium Catalysis 癸钨酸盐与铬催化相结合实现 1,3-丁二烯的氧化还原中性 1,2-二碳化反应
Synthesis Pub Date : 2024-05-15 DOI: 10.1055/a-2328-3037
D. Ding, Pu-Sheng Wang
{"title":"Redox-Neutral 1,2-Dicarbonfunctionlization of 1,3-Butadiene by Merging Decatungstate and Chromium Catalysis","authors":"D. Ding, Pu-Sheng Wang","doi":"10.1055/a-2328-3037","DOIUrl":"https://doi.org/10.1055/a-2328-3037","url":null,"abstract":"Homoallylic alcohol is a significantly useful intermediate in organic synthesis. Here we establish a three-component NHK-type reaction of 1,3-butadiene, aldehydes and aliphatic C–H partners by merging decatungstate and chromium catalysis, enabling a modular, redox-neutral and atom-economic strategy to access a diverse range of homoallylic alcohols.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"136 27","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140976887","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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