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A multi-stimuli responsive spiropyran-tetraphenylethene conjugate for the control of near-infrared emission 用于控制近红外发射的多刺激响应螺吡喃-四苯基噻吩共轭物
Synthesis Pub Date : 2024-08-08 DOI: 10.1055/a-2383-0905
Sajal Kar, Sheelbhadra Chatterjee, S. Bandyopadhyay
{"title":"A multi-stimuli responsive spiropyran-tetraphenylethene conjugate for the control of near-infrared emission","authors":"Sajal Kar, Sheelbhadra Chatterjee, S. Bandyopadhyay","doi":"10.1055/a-2383-0905","DOIUrl":"https://doi.org/10.1055/a-2383-0905","url":null,"abstract":"The synthesis of a dinitrotetraphenylethene linked to two photochromic spiropyran moeities was achieved. The compound displays photochromic and acidochrmic behavior. In the aggregated merocyanine photoisomeric state, the molecule is prone to form aggregates of the zwitterionic form. The merocyanine form displays near-infrared intense fluorescence (λmax_em. at 665 nm) extending into the near-infrared region up to 900 nm. On the other hand, the spiropyran form displays fluorescence in the 450 nm region. In DMF water-mixture, the near-infrared emission is quenched whereas the spiropyran form displays fluorescence with a λmax_em. at 563 nm.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141926484","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
Practical Synthesis of N-anilinyl phenothiazines using a cyclic hypervalent iodine coupling reagent 使用环状高价碘偶联试剂合成 N-苯胺基吩噻嗪的实用方法
Synthesis Pub Date : 2024-08-08 DOI: 10.1055/a-2383-0958
Kana Yanase, K. Morimoto, T. Dohi, Y. Kita
{"title":"Practical Synthesis of N-anilinyl phenothiazines using a cyclic hypervalent iodine coupling reagent","authors":"Kana Yanase, K. Morimoto, T. Dohi, Y. Kita","doi":"10.1055/a-2383-0958","DOIUrl":"https://doi.org/10.1055/a-2383-0958","url":null,"abstract":"An improved protocol for the synthesis of N-anilinylphenothiazines based on the coupling reaction of anilines with phenothiazines using cyclic iodine(III) reagents is presented in this study. In the improved method, the product can be isolated and purified without using column chromatography, and the cyclic hypervalent iodine reagent can be quantitatively recovered by aliquot manipulation. Our workup procedure is simpler compared to previously reported ones, facilitating large-scale synthesis. We also successfully performed the para-selective phenothiazination of nitrogen-containing heterocycles such as hydroquinoline, which is important in pharmacology.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141926991","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
PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone Pyrazolo[3,4-b]piperidinones PIFA 介导的苯酚系 1,2-二唑分子内脱芳作用：螺环己二烯酮吡唑并[3,4-b]哌啶酮的合成
Synthesis Pub Date : 2024-08-08 DOI: 10.1055/a-2382-9631
Pradeep Natarajan, Pratibha Bachhley, Sweta Tripathy, Ashok Vasantharaj P, S. Peruncheralathan
{"title":"PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone Pyrazolo[3,4-b]piperidinones","authors":"Pradeep Natarajan, Pratibha Bachhley, Sweta Tripathy, Ashok Vasantharaj P, S. Peruncheralathan","doi":"10.1055/a-2382-9631","DOIUrl":"https://doi.org/10.1055/a-2382-9631","url":null,"abstract":"In recent years, the significance of spirocyclic motifs in drug discovery has increased, owing to their unique ability to engage biological targets. We present the first example of PIFA-mediated dearomative spirocyclization of phenol-tethered pyrazoles, highlighting intramolecular trapping by the pyrazole moiety. This method efficiently affords a variety of spirocyclohexadienone pyrazolo[3,4-b]piperidinones with yields of up to 82%. Mechanistic studies reveal that the dearomatization process involves a cationic intermediate.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141927882","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
1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide to Thiocyanates: An Efficient and Eco-Friendly Synthesis of N-Aryl-2-((3-aryl-1,2,4-oxadiazol-5-yl)thio)acetamides 氧化腈与硫氰酸盐的 1,3-二极环加成反应：一种高效且环保的 N-芳基-2-((3-芳基-1,2,4-恶二唑-5-基)硫)乙酰胺合成方法
Synthesis Pub Date : 2024-08-06 DOI: 10.1055/s-0043-1775390
Vamshikrishna Y. Radhakrishna, Gopal L. Khatik, Vipin A. Nair
{"title":"1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide to Thiocyanates: An Efficient and Eco-Friendly Synthesis of N-Aryl-2-((3-aryl-1,2,4-oxadiazol-5-yl)thio)acetamides","authors":"Vamshikrishna Y. Radhakrishna, Gopal L. Khatik, Vipin A. Nair","doi":"10.1055/s-0043-1775390","DOIUrl":"https://doi.org/10.1055/s-0043-1775390","url":null,"abstract":"<p>An efficient and eco-friendly procedure was developed for the synthesis of <i>N</i>-aryl-2-((3-aryl-1,2,4-oxadiazol-5-yl)thio)acetamides from <i>N</i>-aryl-2-thiocyanatoacetamides and substituted <i>N</i>-hydroxybenzimidoyl chlorides that were prepared easily from the commercially available anilines and aryl aldehydes, respectively. The <i>N</i>-aryl-2-thiocyanatoacetamide acts as a dipolarophile while the nitrile oxide formed <i>in situ</i> from substituted <i>N</i>-hydroxybenzimidoyl chloride acts as the nucleophilic partner in a 1,3-dipolar cycloaddition reaction mediated by triethylamine base in ethanol medium. The procedure affords excellent yields of desired products containing electron-withdrawing and electron-donating groups on the aromatic rings, in short reaction time with ease of operation. The procedure for the synthesis of scaffolds that are potentially valuable for their biological properties also offers the possibility of scale-up to higher quantities.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141932949","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
Oxidation of Eugenol Derivatives with KMnO4 and CrO3 用 KMnO4 和 CrO3 氧化丁香酚衍生物
Synthesis Pub Date : 2024-08-05 DOI: 10.1055/s-0043-1775032
Achraf Abdou, Fatima Ezzahra Maaghloud, Nikolay Tumanov, Johan Wouters, Jamal JamalEddine, Abdelhakim Elmakssoudi, Mohamed Dakir
{"title":"Oxidation of Eugenol Derivatives with KMnO4 and CrO3","authors":"Achraf Abdou, Fatima Ezzahra Maaghloud, Nikolay Tumanov, Johan Wouters, Jamal JamalEddine, Abdelhakim Elmakssoudi, Mohamed Dakir","doi":"10.1055/s-0043-1775032","DOIUrl":"https://doi.org/10.1055/s-0043-1775032","url":null,"abstract":"<p>This study aims to delineate the synthesis of eugenol derivatives, starting with hydroxyl group protection and then the subsequent oxidation stages. Initially, eugenol underwent conversion into acetyleugenol and benzyleugenol during the protection phase. Subsequently, a kinetic oxidation of acetyleugenol with KMnO<sub>4</sub> via GC-MS analysis resulted in the identification of four compounds. The kinetic investigation indicated the primary formation of diolacetyleugenol, succeeded by aldehyde eugenol, which further gets converted into its respective carboxylic acid. Additionally, acetyleugenol and benzyleugenol underwent oxidation with CrO<sub>3</sub>, yielding the corresponding carboxylic acids.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141932950","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
Recent Advances in Saturated N-Heterocycle C–H Bond Functionalization for Alkylated N-Heterocycle Synthesis 饱和 N-杂环 C-H 键官能化用于烷基化 N-杂环合成的最新进展
Synthesis Pub Date : 2024-08-01 DOI: 10.1055/s-0043-1775377
Cameron H. M. Zheng, Laurel L. Schafer
{"title":"Recent Advances in Saturated N-Heterocycle C–H Bond Functionalization for Alkylated N-Heterocycle Synthesis","authors":"Cameron H. M. Zheng, Laurel L. Schafer","doi":"10.1055/s-0043-1775377","DOIUrl":"https://doi.org/10.1055/s-0043-1775377","url":null,"abstract":"<p>The prominence of saturated <i>N</i>-heterocycle motifs in pharmaceuticals is undeniable. Challenges associated with the alkylation of saturated <i>N</i>-heterocycle scaffolds to efficiently access new drug analogues are hampered by synthetically laborious routes. Stereocontrolled alkyl-substitutions onto saturated <i>N</i>-heterocycles are particularly difficult to access in high yields by traditional synthetic methods. Alternatively, C–H bond functionalization provides a new and powerful synthetic avenue by directly and selectively functionalizing/alkylating/ arylating the abundantly available C–H bonds of saturated <i>N</i>-heterocycles. This review highlights complementary methods for directly activating and functionalizing C–H bonds of saturated <i>N</i>-heterocycles chemo-, regio-, and or stereoselectively to access alkylated products. This synthetic challenge has required catalyst development to access useful <i>N</i>-heterocyclic building blocks or for late-stage functionalization. Early transition metal, late transition metal, photoredox, and electrochemical methods are discussed. The selective functionalization of α, β, and γ C–H bonds to form new C–C, C–N, C–O, and C–B bonds is presented.</p> <p>1 Introduction</p> <p>2 Early Transition Metal Catalyzed α-Alkylation</p> <p>3 Late Transition Metal Catalyzed α-Functionalization</p> <p>4 Photoredox-Catalyzed α-Functionalization</p> <p>5 Electrochemical α-Functionalization</p> <p>6 C–H Functionalization of β and γ C–H Bonds</p> <p>7 Conclusions/Outlook</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141884559","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
Advances in Photoinduced Minisci-like Reactions 光诱导迷你型反应的研究进展
Synthesis Pub Date : 2024-07-29 DOI: 10.1055/s-0043-1775387
Mario Martos, Irene Bosque, Jose C. Gonzalez-Gomez
{"title":"Advances in Photoinduced Minisci-like Reactions","authors":"Mario Martos, Irene Bosque, Jose C. Gonzalez-Gomez","doi":"10.1055/s-0043-1775387","DOIUrl":"https://doi.org/10.1055/s-0043-1775387","url":null,"abstract":"<p>The Minisci reaction, which has been around for more than five decades, is still the preferred tool for the straightforward alkylation of basic heteroarenes. The recent developments in photocatalysis have opened novel pathways for radical generation under milder and more sustainable conditions. Implementing this approach into the Minisci reaction has renewed interest in this transformation, which is attractive per se in Medicinal Chemistry. Aspects such as sacrificial oxidants, catalysts, and specific reaction conditions should be carefully examined to evaluate the practicability of the protocol. This short review focuses on recent advances (2020 to February 2024) in photoinduced Minisci-type reactions, emphasizing sustainability.</p> <p>1 Introduction</p> <p>2 Using Noble-Metal-Based Photocatalysts</p> <p>3 Noble-Metal-Free Methods Using Sacrificial Oxidants</p> <p>4 Noble-Metal-Free Methods Without Sacrificial Oxidants</p> <p>5 Conclusions and Perspectives</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141872989","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
Magnesium-Mediated Regioselective Additions of Bromoform to Quinone Methides and Aurone-Derived Azadienes 镁介导的溴甲烷与醌甲醚和曙红衍生二氮苯的区域选择性加成反应
Synthesis Pub Date : 2024-07-25 DOI: 10.1055/a-2353-1722
Deepak Kumar, Nishikant Satam, Irishi N. N. Namboothiri
{"title":"Magnesium-Mediated Regioselective Additions of Bromoform to Quinone Methides and Aurone-Derived Azadienes","authors":"Deepak Kumar, Nishikant Satam, Irishi N. N. Namboothiri","doi":"10.1055/a-2353-1722","DOIUrl":"https://doi.org/10.1055/a-2353-1722","url":null,"abstract":"<p>The magnesium-mediated addition of bromoform to conjugated electron-deficient alkenes and imines, such as <i>para</i>-quinone methides (<i>p</i>-QMs) and aurone-derived azadienes, respectively, is reported here for the first time. While <i>p</i>-QMs undergo exclusive and hitherto unreported 1,6-addition of bromoform to afford benzylic tribromomethylated diarylmethanes, aurone-derived azadienes undergo both 1,2- and 1,4-additions to furnish α- and γ-tribromomethylamines. A mechanism involving the intermediacy of the tribromomethyl radical has been proposed based on control experiments and EPR studies. Representative synthetic transformations have also been carried out.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141782553","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
Regio- and Chemoselective Synthesis of 4,6-Dithia-1,2,9-triazaspiro[4.4]non-2-en-8-ones through an Ultrasound-Promoted One-Pot Sequential Pseudo-Five-Component Reaction 通过超声波促进的单锅顺序伪五组分反应，实现 4,6-二硫杂-1,2,9-三氮杂螺[4.4]壬-2-烯-8-酮的区域和化学选择性合成
Synthesis Pub Date : 2024-07-22 DOI: 10.1055/s-0043-1775386
Abdolali Alizadeh, Ebrahim Amir Chelebari, Reza Rezaiyehraad
{"title":"Regio- and Chemoselective Synthesis of 4,6-Dithia-1,2,9-triazaspiro[4.4]non-2-en-8-ones through an Ultrasound-Promoted One-Pot Sequential Pseudo-Five-Component Reaction","authors":"Abdolali Alizadeh, Ebrahim Amir Chelebari, Reza Rezaiyehraad","doi":"10.1055/s-0043-1775386","DOIUrl":"https://doi.org/10.1055/s-0043-1775386","url":null,"abstract":"<p>Spiro-heterocycles have attracted significant interest due to their unique biological properties with fewer side effects compared to traditional drugs. Herein, a novel method is reported for the synthesis of a series of spiro-heterocycles possessing a quinoline motif. The strategy utilizes rhodanine derivatives, hydrazonoyl chlorides, and 2-chloroquinoline-3-carbaldehyde, and proceeds via a one-pot sequential pseudo-five-component reaction. The reactions are found to proceed in a regioselective and chemoselective manner. </p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141782561","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
Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold 氨基糖的立体选择性合成路线：利用通用多功能手性支架的不同方法
Synthesis Pub Date : 2024-07-22 DOI: 10.1055/a-2353-1618
Srinath Pashikanti, Apurba Datta
{"title":"Stereoselective Synthetic Routes to Iminosugars: A Divergent Approach Utilizing a Common Multifunctional Chiral Scaffold","authors":"Srinath Pashikanti, Apurba Datta","doi":"10.1055/a-2353-1618","DOIUrl":"https://doi.org/10.1055/a-2353-1618","url":null,"abstract":"<p>Starting from an l-serine-derived multifunctional aminobutenolide as a common chiral building block, stereoselective synthetic routes to representative examples of di-, tri-, and tetrahydroxylated iminosugars have been developed. Key steps in the synthetic routes involved an intramolecular aminolysis protocol to form the azaheterocyclic core, and functionalization of a resident alkene moiety towards installation of the desired substituents at the various positions of the piperidine ring. The strategy and the approach described are expected to provide flexible synthetic routes to various iminosugar scaffolds of structural and medicinal chemical significance.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141782552","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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