Silver-Catalyzed Cascade Cyclization of Amino-NH-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles

An operationally simple Ag(I)-catalyzed approach for the synthesis of isoquinoline and quinazoline fused 1,2,3-triazoles was developed by a condensation and amination cyclization cascade of amino-NH-1,2,3-triazoles with 2-alkynylbenzaldehydes involving three new C-N bond formations in one manipulation, in which the group of -NH of the triazole ring serves as a nucleophile to form the quinazoline skeleton. The efficient protocol can be applied to a variety of substrates containing a range of functional groups, delivering novel pentacyclic fused 1,2,3-triazoles in good-to-excellent yields.

[1]  Zihao Xia,et al.  Oleanane-Type Triterpene Conjugates with 1H-1,2,3-Triazole Possessing of Fungicidal Activity , 2022, Molecules.

[2]  A. Salem,et al.  New 1,2,3-triazole linked ciprofloxacin-chalcones induce DNA damage by inhibiting human topoisomerase I& II and tubulin polymerization , 2022, Journal of enzyme inhibition and medicinal chemistry.

[3]  K. N. Venugopala,et al.  1,2,3-Triazolyl-tetrahydropyrimidine Conjugates as Potential Sterol Carrier Protein-2 Inhibitors: Larvicidal Activity against the Malaria Vector Anopheles arabiensis and In Silico Molecular Docking Study , 2022, Molecules.

[4]  Shrey Desai,et al.  Borinic Acid Catalyzed Regioselective N-Alkylation of Azoles. , 2022, The Journal of organic chemistry.

[5]  M. Çiçek,et al.  Design, synthesis and biological evaluation of 8-aminoquinoline-1,2,3-triazole hybrid derivatives as potential antimicrobial agents , 2022, Medicinal Chemistry Research.

[6]  P. Beier,et al.  Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles. , 2022, Organic letters.

[7]  Hamada S. Abulkhair,et al.  Apoptosis induction, PARP-1 inhibition, and cell cycle analysis of leukemia cancer cells treated with novel synthetic 1,2,3-triazole-chalcone conjugates. , 2022, Bioorganic chemistry.

[8]  Guilherme M. Bousada,et al.  Synthesis of Tyrosol 1,2,3-Triazole Derivatives and Their Phytotoxic Activity against Euphorbia heterophylla. , 2022, Journal of agricultural and food chemistry.

[9]  Martin Gazvoda,et al.  Copper-Catalyzed Azide–Alkyne Cycloaddition of Hydrazoic Acid Formed In Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles , 2022, The Journal of organic chemistry.

[10]  D. Rawat,et al.  Magnetically Separable Fe3O4@poly(m‐phenylenediamine)@Cu2O Nanocatalyst for the Facile Synthesis of 5‐phenyl‐[1,2,3]triazolo[1,5‐c]quinazolines , 2022, ChemCatChem.

[11]  G. Deng,et al.  Copper-catalyzed three-component N-alkylation of quinazolinones and azoles. , 2022, Organic & biomolecular chemistry.

[12]  Sarvesh S. Harmalkar,et al.  1,6-Addition of 1,2,3-NH triazoles to para-quinone methides: Facile access to highly selective N1 and N2 substituted triazoles. , 2021, Organic & biomolecular chemistry.

[13]  D. Nguyen,et al.  Robust Water-Soluble Gold Nanoparticles via Polymerized Mesoionic N-Heterocyclic Carbene–Gold(I) Complexes , 2021, Chemistry of Materials.

[14]  R. C. Duarte,et al.  Anti-inflammatory, ulcerogenic and platelet activation evaluation of novel 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids. , 2021, Bioorganic chemistry.

[15]  M. Kumari,et al.  A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry , 2021, Chemical biology & drug design.

[16]  Minghao Li,et al.  Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis , 2021, Green Chemistry.

[17]  Tao Wang,et al.  Access to (Z)-β-Substituted Enamides from N1-H-1,2,3-Triazoles. , 2021, Organic letters.

[18]  Deli Chen,et al.  Substituted 1,2,3-triazoles: a new class of nitrification inhibitors , 2021, Scientific Reports.

[19]  V. Ferreira,et al.  Bioactive 1,2,3‐Triazoles: An Account on their Synthesis, Structural Diversity and Biological Applications , 2021, Chemical record.

[20]  B. Ernst,et al.  Does targeting Arg98 of FimH lead to high affinity antagonists? , 2020, European journal of medicinal chemistry.

[21]  Lihong Shan,et al.  Synthesis of [1,2,3]‐Triazolo[5,1‐ a ]‐isoquinolines through TBAF‐Promoted Cascade Reactions , 2020 .

[22]  Yubo Jiang,et al.  Metal‐Free, Visible‐Light Promoted Intramolecular Azole C−H Bond Amination Using Catalytic Amount of I 2 : A Route to 1,2,3‐Triazolo[1,5‐ a ]quinazolin‐5(4 H )‐ones , 2020 .

[23]  Yubo Jiang,et al.  Copper-catalyzed cross-coupling and sequential allene-mediated cyclization for the synthesis of 1,2,3-triazolo[1,5-a]quinolines. , 2020, Organic & biomolecular chemistry.

[24]  Mingming Ma,et al.  Cu-Catalyzed Site-Selective and Enantioselective Ring Opening of Cyclic Diaryliodoniums with 1,2,3-Triazoles. , 2020, Organic letters.

[25]  E. Anderson,et al.  Copper-Catalyzed Intramolecular C-H Alkoxylation of Diaryltriazoles: Synthesis of Tricyclic Triazole Benzoxazines. , 2020, Organic letters.

[26]  Igor D. Jurberg,et al.  Blue Light‐Promoted N−H Insertion of Carbazoles, Pyrazoles and 1,2,3‐Triazoles into Aryldiazoacetates , 2020 .

[27]  Siyu Ye,et al.  Efficient and Divergent Synthesis of Medium‐Sized Lactams through Zinc‐Catalyzed Oxidative Cyclization of Indoly Ynamides † , 2020 .

[28]  Yahui Wang,et al.  Diamine-mediated N2-selective β-selenoalkylation of triazoles with alkenes. , 2020, Chemical communications.

[29]  P. Zhan,et al.  Design, synthesis and structure-activity relationships of 4-phenyl-1H-1,2,3-triazole phenylalanine derivatives as novel HIV-1 capsid inhibitors with promising antiviral activities. , 2020, European journal of medicinal chemistry.

[30]  Jianliang Yu,et al.  Scandium-catalyzed highly selective N2-alkylation of benzotriazoles with cyclohexanones , 2020 .

[31]  Xi Jia Ai Ti Re He Man,et al.  Highly N2-selective allylation of NH-1,2,3-triazoles with allenamides mediated by N-iodosuccinimide , 2019, New Journal of Chemistry.

[32]  Guiping Qin,et al.  Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles , 2019, Synlett.

[33]  B. Török,et al.  Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination , 2019, Green Chemistry.

[34]  M. Koketsu,et al.  Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes , 2018, Synthesis.

[35]  J. Nanubolu,et al.  Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates , 2018 .

[36]  M. Bassetti,et al.  Ceftolozane/tazobactam: place in therapy. , 2018 .

[37]  B. Breit,et al.  Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Triazoles with Internal Alkynes and Terminal Allenes. , 2018, Organic letters.

[38]  R. Peddinti,et al.  Asymmetric Organocatalytic Approach to 2,4-Disubstituted 1,2,3-Triazoles by N2-Selective Aza-Michael Addition. , 2018, The Journal of organic chemistry.

[39]  G. Rastelli,et al.  The 1,2,3-triazole ring as a bioisostere in medicinal chemistry. , 2017, Drug discovery today.

[40]  Zhi Xu,et al.  Triazole derivatives and their anti-tubercular activity. , 2017, European journal of medicinal chemistry.

[41]  R. Peddinti,et al.  Regiospecific Aza-Michael Addition of 4-Aryl-1H-1,2,3-triazoles to Chalcones: Synthesis of 2,4-Disubstituted 1,2,3-Triazoles in Basic Medium , 2017, Synlett.

[42]  Qionglin Liang,et al.  Recyclable Acid–Base Bifunctional Core–Shell–Shell Nanosphere Catalyzed Synthesis of 5‐Aryl‐1H‐1,2,3‐triazoles through the “One‐Pot” Cyclization of Aldehydes, Nitromethane, and Sodium Azide , 2017 .

[43]  R. Peddinti,et al.  Base-Mediated Ring Opening of meso-Epoxides with 4-Aryl-NH-1,2,3-triazoles: Synthesis of trans-2-(Aryltriazolyl)cycloalkanols , 2017, Synthesis.

[44]  Gang Nie,et al.  Copper-Catalyzed Cross-Dehydrogenative N2-Coupling of NH-1,2,3-Triazoles with N,N -Dialkylamides: N-Amidoalkylation of NH-1,2,3-Triazoles. , 2017, The Journal of organic chemistry.

[45]  Zili Chen,et al.  Post-synthetic modification of tryptophan containing peptides via NIS mediation. , 2017, Organic & biomolecular chemistry.

[46]  Yubo Jiang,et al.  Silver-Catalyzed Intramolecular C(5)–H Acyloxylation of 1,4-Disubstituted 1,2,3-Triazoles , 2017, Synlett.

[47]  Virender Singh,et al.  Medicinal attributes of 1,2,3-triazoles: Current developments. , 2017, Bioorganic chemistry.

[48]  Hengshan Wang,et al.  Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide–alkene cascade reaction , 2017 .

[49]  R. Peddinti,et al.  DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles , 2017 .

[50]  Zili Chen,et al.  N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles. , 2016, The Journal of organic chemistry.

[51]  Wei Chen,et al.  Carboxyamidotriazole inhibits oxidative phosphorylation in cancer cells and exerts synergistic anti-cancer effect with glycolysis inhibition. , 2016, Cancer letters.

[52]  Keqin Deng,et al.  CuI-catalyzed domino reactions for the synthesis of benzoxazine-fused isoquinolines under microwave irradiation , 2016 .

[53]  Min-Min Tang,et al.  Synthesis of Isoquinolines Derivatives from o-Alkynyl Aldehydes , 2016 .

[54]  A. Wu,et al.  Consecutive Cycloaddition/S(N)Ar/Reduction/Cyclization/Oxidation Sequences: A Copper-Catalyzed Multicomponent Synthesis of Fused N-Heterocycles. , 2015, Organic letters.

[55]  Zhen Wang,et al.  Highly N2-selective coupling of 1,2,3-triazoles with indole and pyrrole. , 2014, Chemistry.

[56]  P. Yin,et al.  1,2,3-Triazolo[4,5,-e]furazano[3,4,-b]pyrazine 6-oxide--a fused heterocycle with a roving hydrogen forms a new class of insensitive energetic materials. , 2014, Chemistry.

[57]  P. Yogeeswari,et al.  Design, synthesis and evaluation of 6-(4-((substituted-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)phenanthridine analogues as antimycobacterial agents. , 2013, Bioorganic & medicinal chemistry letters.

[58]  Xiaodong Shi,et al.  A facile synthesis of 5-amino-[1,2,3]triazolo[5,1-a]isoquinoline derivatives through copper-catalyzed cascade reactions. , 2013, Organic & biomolecular chemistry.

[59]  R. Ummanni,et al.  Electrophile induced branching cascade: a powerful approach to access various molecular scaffolds and their exploration as novel anti-mycobacterial agents. , 2013, Chemical Communications.

[60]  Shi-jian Su,et al.  A Series of New Medium‐Bandgap Conjugated Polymers Based on Naphtho[1,2‐c:5,6‐c]bis(2‐octyl‐[1,2,3]triazole) for High‐Performance Polymer Solar Cells , 2013, Advanced materials.

[61]  A. Verma,et al.  On water: silver-catalyzed domino approach for the synthesis of benzoxazine/oxazine-fused isoquinolines and naphthyridines from o-alkynyl aldehydes. , 2013, The Journal of organic chemistry.

[62]  Hualiang Jiang,et al.  ‘One-pot’ Synthesis of Dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinolines via a Silver(I)-Catalyzed Cascade Approach , 2013, Molecules.

[63]  A. Verma,et al.  AgI‐Catalyzed Cascade Strategy: Regioselective Access to Diversely Substituted Fused Benzimidazo[2,1‐a]isoquinolines, Naphthyridines, Thienopyridines, and Quinoxalines in Water , 2012 .

[64]  V. Zoete,et al.  Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition. , 2012, Journal of medicinal chemistry.

[65]  Xiaodong Shi,et al.  Mitsunobu reaction of 1,2,3-NH-triazoles: a regio- and stereoselective approach to functionalized triazole derivatives. , 2011, Chemistry, an Asian journal.

[66]  S. Buchwald,et al.  Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles. , 2011, Angewandte Chemie.

[67]  Nikunj M. Shukla,et al.  Structure-activity relationships in human toll-like receptor 7-active imidazoquinoline analogues. , 2010, Journal of medicinal chemistry.

[68]  Anil Kumar Mutyala,et al.  Facile Assembly of Fused Isoquinolines by Gold(I)‐Catalyzed Coupling–Cyclization Reactions between o‐Alkynylbenzaldehydes and Aromatic Amines Containing Tethered Nucleophiles , 2010 .

[69]  S. Walker,et al.  Development of improved inhibitors of wall teichoic acid biosynthesis with potent activity against Staphylococcus aureus. , 2010, Bioorganic & medicinal chemistry letters.

[70]  Deqing Shi A Convenient Synthesis of 3-(Substituted pyridyl (or thiazolyl)methyl)- 1,2,3-triazolo(4,5-d)pyrimidin-7-one via the Tandem Aza-Wittig Reaction and Their Herbicidal Activity , 2010 .

[71]  Xiaodong Shi,et al.  Highly efficient synthesis of vinyl substituted triazoles by Au(I) catalyzed alkyne activation. , 2009, Bioorganic & medicinal chemistry letters.

[72]  B. Torbett,et al.  A copper(I)-catalyzed 1,2,3-triazole azide-alkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant. , 2008, Journal of medicinal chemistry.

[73]  Morten Meldal,et al.  Cu-catalyzed azide-alkyne cycloaddition. , 2008, Chemical reviews.

[74]  Amal Al‐Azmi,et al.  Alkylation of azoles: Synthesis of new heterocyclic-based AT1-non-peptide angiotensin (II) receptor antagonists , 2007 .

[75]  C. Valdés,et al.  Developments in Pd catalysis: synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides. , 2006, Angewandte Chemie.

[76]  C. Hawker,et al.  Dendronized linear polymers via "click chemistry". , 2004, Journal of the American Chemical Society.

[77]  Craig J Hawker,et al.  Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes. , 2004, Angewandte Chemie.

[78]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[79]  R. Larock,et al.  Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of o-(1-alkynyl)benzaldimines and organic halides. , 2001, Organic letters.

[80]  Y. Matano,et al.  Photochemical azido ligand transfer reaction of a triarylbismuth diazide with alkynes , 1993 .

[81]  S. D'Andrea,et al.  1,2,3-Triazoles from Z-β-(Formyloxy)vinyl Azides and Triethyl Phosphite. , 1991 .

[82]  Arun K. Ghosh,et al.  1,2,3-TRIAZOLES FROM (Z)-BETA -(FORMYLOXY)VINYL AZIDES AND TRIETHYL PHOSPHITE , 1991 .