Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements.

Heterocyclic chemistry is an ever-expanding field without boundaries. Heterocycles play a significant role in medicinal and pharmaceutical chemistry, the agricultural industry and materials science. Among heterocycles, N-heterocycles constitute a large family. Their ubiquity in living and non-living systems makes them an endless topic for research. Being a part of the research community, we need to balance environmental concerns with scientific and economic development. So, research that is coherent with nature is a trending domain at all times. Silver catalysis possesses a greener face in organic synthesis. The simple, rich and extensive chemistry shown by silver makes it an attractive choice for catalysis. Inspired by its versatility and uniqueness we have compiled here recent developments in the silver-catalyzed synthesis of nitrogen-containing heterocycles since 2019. The high efficiency, regioselectivity, chemoselectivity, recyclability of the catalytic system, greater atom economy and simple reaction setup are the major highlights of this protocol. It is a hot research topic which is evident from the large number of works carried out for the fabrication of a range of N-heterocycles with varying complexities.

[1]  Maxime Hourtoule,et al.  Silver-Catalyzed Domino Reaction of CF3-Substituted N-Allenamides with Primary Amines for the Construction of 2-Amido-5-fluoropyrroles. , 2023, Organic letters.

[2]  Qingyang Zhao,et al.  Silver-Catalyzed Direct Nucleophilic Cyclization: Enantioselective De Novo Synthesis of C-C Axially Chiral 2-Arylindoles. , 2023, Organic letters.

[3]  Yonghui Zhang,et al.  Silver(I)-Catalyzed Oxidative Cyclopropanation of 1,6-Enynes: Synthesis of 3-Aza-bicyclo[3.1.0]hexane Derivatives. , 2022, Organic letters.

[4]  A. Poater,et al.  Intramolecular Interception of the Remote Position of Vinylcarbene Silver Complex Intermediates by C(sp3)−H Bond Insertion , 2022, Angewandte Chemie.

[5]  Yubo Jiang,et al.  Silver-Catalyzed Cascade Cyclization of Amino-NH-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles , 2022, Molecules.

[6]  S. Samanta,et al.  AgOTf/Et3N Cooperative Catalysis Enabled One‐Pot Access to α‐(Indolizinylethyl)‐Substituted N‐Sulfonyl Ketimines via an Imino‐Alkyne Cyclization , 2022, Asian Journal of Organic Chemistry.

[7]  Chada Raji Reddy,et al.  Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids , 2022, ACS omega.

[8]  B. Yildirim,et al.  Green synthesis of silver nanoparticles using Lathyrus brachypterus extract for efficient catalytic reduction of methylene blue, methyl orange, methyl red and investigation of a kinetic model , 2022, Reaction Kinetics, Mechanisms and Catalysis.

[9]  M. Selkti,et al.  Access to Conjugated Enynes via Allenyl Silver Formation/Cyclization/Decarboxylation Reaction Catalyzed by Silver Carbonate(I). , 2022, Organic letters.

[10]  D. Murzin,et al.  Liquid-Phase Oxidation of Betulin Over Supported Ag Nps Catalysts: Kinetic Regularities, Catalyst Deactivation and Reactivation , 2022, SSRN Electronic Journal.

[11]  Tohru Yamada,et al.  Silver-Catalyzed Carbon Dioxide Fixation on Alkynylindoles. , 2022, Organic letters.

[12]  Z. Shao,et al.  Construction of Axially Chiral Indoles by Cycloaddition–Isomerization via Atroposelective Phosphoric Acid and Silver Sequential Catalysis , 2022, ACS Catalysis.

[13]  Linghui Qian,et al.  Simultaneous Construction of C-N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3 + 2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides. , 2022, Organic letters.

[14]  M. Kärkäs,et al.  Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones , 2022, Organic letters.

[15]  S. Joshi,et al.  Synthesis, Characterization and Molecular Docking of Novel Lonazolac Analogues 3-(3-Hydroxy-5-methyl-1H-pyrazol-4-yl)-3-arylpropanoic Acid Derivatives: Highly Potential COX-1/COX-2, Matrix Metalloproteinase and Protein Denaturation Inhibitors , 2022, Journal of Molecular Structure.

[16]  K. Oh,et al.  Silver-Catalyzed Asymmetric Desymmetrization of Cyclohexadienones via Van Leusen Pyrrole Synthesis. , 2022, Organic letters.

[17]  Xin-Meng Chen,et al.  Ag-Catalyzed Asymmetric Interrupted Barton-Zard Reaction Enabling the Enantioselective Dearomatization of 2- and 3-Nitroindoles. , 2022, Organic letters.

[18]  Xiaoyang Cheng,et al.  Synthesis of Chiral Nine‐Membered N‐Heterocycles through Silver(I)‐Promoted Cycloaddition and Rearrangement from N‐Vinyl‐α,β‐Unsaturated Nitrones with Chiral 3‐Propioloyloxazolidin‐2‐ones , 2021, Advanced Synthesis & Catalysis.

[19]  B. Deka,et al.  Ten Years of Glory in the α-Functionalizations of Acetophenones: Progress Through Kornblum Oxidation and C–H Functionalization , 2021, Topics in Current Chemistry.

[20]  J. C. Cunha,et al.  Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles , 2021, Catalysts.

[21]  Wei Zhong,et al.  Multifunctional Ag(I)/CAAA-Amidphos Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of α-Substituted Acrylamides , 2021 .

[22]  S. Harada,et al.  Stereoselective construction of fused cyclopropane from ynamide and its application to synthesis of small drug candidate molecules , 2021 .

[23]  G. Anilkumar,et al.  Silver‐catalyzed pyrrole synthesis: An overview , 2021 .

[24]  T. Nemoto,et al.  Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis. , 2020, Journal of the American Chemical Society.

[25]  G. Anilkumar,et al.  Recent Advances in the Silver Catalysed Synthesis of Furan and Its Applications , 2020 .

[26]  T. Loh,et al.  Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides , 2020 .

[27]  Changjin Lim,et al.  Preliminary Study on Novel Expedient Synthesis of 5-Azaisocoumarins by Transition Metal-Catalyzed Cycloisomerization , 2020, Frontiers in Chemistry.

[28]  G. Anilkumar,et al.  An Overview of Ag‐catalyzed Synthesis of Six‐membered Heterocycles , 2020 .

[29]  Feng-Lin Hong,et al.  Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis. , 2020, Accounts of chemical research.

[30]  V. Michelet,et al.  Silver-catalyzed intramolecular [4 + 2] cycloaddition reaction of amide-1,6-enynes , 2020 .

[31]  P. Gong,et al.  Silver(I)‐ and Base‐Mediated formal [4+3] Cycloaddition of in Situ generated 1,2‐Diaza‐1,3‐dienes with C,N ‐Cyclic Azomethine Imines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives , 2020 .

[32]  Rajwinder Kaur,et al.  Nitrogen Containing Heterocycles as Anticancer Agents: An Overview. , 2020, Anti-cancer agents in medicinal chemistry.

[33]  M. Liyaghati-Delshad,et al.  Ag–TiO2 nanocomposite as an efficient and recyclable catalyst for the synthesis of imidazole-pyrimidine derivatives in solvent-free conditions , 2020, Monatshefte für Chemie - Chemical Monthly.

[34]  G. Blond,et al.  Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization , 2020, Molecules.

[35]  Minsoo Ju,et al.  Silver-Catalyzed Enantioselective Propargylic C-H Bond Amination Through Rational Ligand Design. , 2020, Journal of the American Chemical Society.

[36]  Kranthi Kumar Gangu,et al.  A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications , 2020, Molecules.

[37]  X. Bi,et al.  Silver-Catalyzed Activation of Terminal Alkynes for Synthesizing Nitrogen-Containing Molecules. , 2020, Accounts of chemical research.

[38]  M. Hasan,et al.  Synthesis of imidazo[1, 2‐a]pyridines via the silver acetate‐catalyzed Groebke‐Blackburn‐Bienayme reaction with ethylene glycol as a biodegradable and sustainable solvent , 2020 .

[39]  Vsevolod A. Peshkov,et al.  Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines , 2020 .

[40]  Chung‐Ming Sun,et al.  Catalyst-Controlled Regioselective Synthesis of Benzotriazlolodiazepin-7-ones and Benzotriazolodiazocin-8-ones. , 2019, Organic letters.

[41]  S. Saranya,et al.  Recent Trends in the Silver‐Catalyzed Synthesis of Nitrogen Heterocycles , 2019, Advanced Synthesis & Catalysis.

[42]  Bing Yu,et al.  Silver‐Catalyzed Radical Cascade Cyclization of Unactivated Alkenes towards Cyclopenta[ c ]quinolines , 2019, Advanced Synthesis & Catalysis.

[43]  J. Yoon,et al.  Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C , 2019, Synthesis.

[44]  A. Moradi,et al.  Silver Nanoparticles Supported on Chitosan as a Green and Robust Heterogeneous Catalyst for Direct Synthesis of Nitrogen Heterocyclic Compounds under Green Conditions , 2019, Bulletin of Chemical Reaction Engineering & Catalysis.

[45]  C. Pask,et al.  Synthesis of oxetane/azetidine containing spirocycles , 2019, Tetrahedron Letters.

[46]  R. Luque,et al.  Heterogeneously Catalyzed Synthesis of Imidazolones via Cycloisomerizations of Propargylic Ureas Using Ag and Au/Al SBA-15 Systems , 2019, ACS Sustainable Chemistry & Engineering.

[47]  Chao‐Jun Li,et al.  Silver Catalysis in Organic Synthesis , 2019 .

[48]  J. Khalafy,et al.  A simple protocol for the green synthesis of a new series of pyrimido[4,5-b][1,6]naphthyridines in the presence of silver nanoparticles (AgNPs) , 2018, Arkivoc.

[49]  M. Porter,et al.  Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines. , 2018, Journal of the American Chemical Society.

[50]  Lei Zhou,et al.  Synthesis of N-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis. , 2016, Chemical record.

[51]  A. R. Fernandes,et al.  Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine’s Tool Box , 2015, Molecules.

[52]  A. Geronikaki,et al.  Selected heterocyclic compounds as antioxidants. Synthesis and biological evaluation. , 2014, Current topics in medicinal chemistry.

[53]  J. Vors,et al.  Synthesis of diversely fluorinated pyrazoles as novel active agrochemical ingredients , 2013 .

[54]  J. Dinges,et al.  Bioactive Heterocyclic Compound Classes: Agrochemicals , 2012 .

[55]  Jiande D. Z. Chen,et al.  Send Orders of Reprints at Reprints@benthamscience.org Rimonabant, Gastrointestinal Motility and Obesity , 2022 .

[56]  A. Gomtsyan,et al.  Heterocycles in drugs and drug discovery , 2012, Chemistry of Heterocyclic Compounds.

[57]  B. B. Mishra,et al.  Natural products: an evolving role in future drug discovery. , 2011, European journal of medicinal chemistry.

[58]  A. Katritzky,et al.  Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications , 2011 .

[59]  N. Kishore,et al.  A novel antifungal anthraquinone from seeds of Aegle marmelos Correa (family Rutaceae). , 2010, Fitoterapia.

[60]  N. Kishore,et al.  Alkaloids as potential anti-tubercular agents. , 2009, Fitoterapia.

[61]  L. Bedoya,et al.  Anti-HIV activity of stilbene-related heterocyclic compounds. , 2006, Bioorganic & medicinal chemistry letters.

[62]  A. V. Karnik,et al.  Synthesis and in vitro antibacterial activity of novel heterocyclic derivatives of 18-nor-equilenin. , 2006, European journal of medicinal chemistry.

[63]  J. Gut,et al.  Synthesis and antimalarial activity of sulfonamide chalcone derivatives. , 2005, Farmaco.

[64]  Louise J K Durling,et al.  A comparison of genotoxicity between three common heterocyclic amines and acrylamide. , 2005, Mutation research.

[65]  T. Torroba,et al.  Special Issue: Sulfur-Nitrogen Heterocycles , 2005, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[66]  E. G. Brown.  Ring Nitrogen and Key Biomolecules , 1998, Springer Netherlands.

[67]  L. Berrino,et al.  Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazo[1,2-a]pyrimidine derivatives , 1994 .