Synthesis of organoselenyl isoquinolinium imides via iron(III) chloride-mediated tandem cyclization/selenation of N'-(2-alkynylbenzylidene)hydrazides and diselenides.

This report describes the synthesis of organoselenyl isoquinolinium imides through a tandem cyclization between N'-(2-alkynylbenzylidene)hydrazides and diselenides. The reaction was carried out at room temperature under an ambient atmosphere using cheap iron(iii) chloride as the metallic source. The strategy shows good tolerance to a broad range of N'-(2-alkynylbenzylidene)hydrazides and diselenides, and forms C-N and C-Se bonds in one step. The obtained product is further transformed into a bioactive H-pyrazolo[5,1-a]isoquinoline skeleton easily via a silver catalyzed [3 + 2] cycloaddition.

[1]  D. Back,et al.  Synthesis of Selenochromenes via Dehydration of Arylalkynols Promoted by Iron(III) Chloride and Diorganyl Diselenides. , 2020, The Journal of organic chemistry.

[2]  Shun-Yi Wang,et al.  Iron(iii) chloride-promoted cyclization of α,β-alkynic tosylhydrazones with diselenides: synthesis of 4-(arylselanyl)-1H-pyrazoles. , 2020, Organic & biomolecular chemistry.

[3]  Yu-Yuan Hei,et al.  Copper-catalyzed direct C–H phosphorylation of N-imino isoquinolinium ylides with H-phosphonates , 2019, Organic Chemistry Frontiers.

[4]  D. Back,et al.  Iron(III) Chloride/Dialkyl Diselenides‐Promoted Cascade Cyclization of ortho ‐Diynyl Benzyl Chalcogenides , 2019, Advanced Synthesis & Catalysis.

[5]  Z. Zhenhua,et al.  Formal [5+3] Cycloaddition of Zwitterionic Allylpalladium Intermediates with Azomethine Imines for Construction of N,O‐Containing Eight‐Membered Heterocycles , 2018 .

[6]  W. Xiao,et al.  Silver(I)- and Base-Mediated [3 + 3]-Cycloaddition of C,N-Cyclic Azomethine Imines with Aza-oxyallyl Cations. , 2018, Organic letters.

[7]  A. Studer,et al.  Radical cascade cyclization of 1,n-enynes and diynes for the synthesis of carbocycles and heterocycles. , 2017, Chemical Society reviews.

[8]  D. Back,et al.  Sequential Carbon-Carbon/Carbon-Selenium Bond Formation Mediated by Iron(III) Chloride and Diorganyl Diselenides: Synthesis and Reactivity of 2-Organoselenyl-Naphthalenes. , 2017, The Journal of organic chemistry.

[9]  D. Back,et al.  Iron(III) Chloride and Diorganyl Diselenide-Promoted Nucleophilic Closures of 1-Benzyl-2-alkynylbenzenes in the Preparation of 9-(Organoselanyl)-5H-benzo[7]annulenes , 2016 .

[10]  Jia-Wu Huang,et al.  Organoselenium-Catalyzed Synthesis of Oxygen- and Nitrogen-Containing Heterocycles. , 2016, Organic letters.

[11]  Jie Wu,et al.  Synthesis of pyrazolo[5,1-a]isoquinolines via a silver(I)-catalyzed reaction of (1-arylethylidene)hydrazides with N'-(2-alkynylbenzylidene)hydrazides. , 2015, Organic & biomolecular chemistry.

[12]  Shun-Yi Wang,et al.  Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines. , 2015, Chemical communications.

[13]  F. Glorius,et al.  Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction , 2015, Nature Chemistry.

[14]  Xiao-Qiang Hu,et al.  Formal [4+1] annulation reactions in the synthesis of carbocyclic and heterocyclic systems. , 2015, Chemical reviews.

[15]  D. Back,et al.  Iron(III) Chloride/Diorganyl Diselenides Promoted Regio‐ and Stereoselective Cyclization of ortho‐Alkynylanilides: Synthesis of (Z)‐4‐(chalcogen)methylenebenzoxazines , 2014 .

[16]  T. Weber,et al.  Direct oxidative allylic and vinylic amination of alkenes through selenium catalysis. , 2013, Angewandte Chemie.

[17]  Benhur Godoi,et al.  Iron(III) chloride/diorganyl diselenides: a tool for intramolecular cyclization of alkynone O-methyloximes. , 2013, The Journal of organic chemistry.

[18]  F. Shi,et al.  Cycloaddition of N-Sulfonylpyridinium Imides and Isoquinolinium Imides with Acetylenedicarboxylates: A Practical Synthesis of Pyrazolo[1,5-a]pyridine and Pyrazolo[5,1-a]isoquinoline Derivatives , 2012 .

[19]  R. Larock,et al.  Synthesis of pyrido[1,2-b]indazoles via aryne [3 + 2] cycloaddition with N-tosylpyridinium imides. , 2011, The Journal of organic chemistry.

[20]  R. Guo,et al.  Iron salt, a cheap, highly efficient and environment-friendly metal catalyst for Se–Se bond cleavage and the further reaction with methylenecyclopropanes under mild conditions , 2011 .

[21]  Jie Wu,et al.  Efficient generation of biologically active H-pyrazolo[5,1-a]isoquinolines via multicomponent reaction. , 2010, Organic letters.

[22]  D. Manna,et al.  Synthesis, structure, spirocyclization mechanism, and glutathione peroxidase-like antioxidant activity of stable spirodiazaselenurane and spirodiazatellurane. , 2010, Journal of the American Chemical Society.

[23]  M. Dolenc,et al.  Advances in the chemistry of saccharins: from synthetic novelties towards biologically active compounds. , 2010, Current medicinal chemistry.

[24]  Andrew C. Terentis,et al.  The selenazal drug ebselen potently inhibits indoleamine 2,3-dioxygenase by targeting enzyme cysteine residues. , 2010, Biochemistry.

[25]  Jie Wu,et al.  Synthesis of functionalized H-pyrazolo[5,1-a]isoquinolines via sequential reactions of N'-(2-alkynylbenzylidene)hydrazides. , 2009, Organic & biomolecular chemistry.

[26]  T. Wirth,et al.  Green chemistry with selenium reagents: development of efficient catalytic reactions. , 2009, Angewandte Chemie.

[27]  Jie Wu,et al.  AgOTf-catalyzed tandem reaction of N'-(2-alkynylbenzylidene)hydrazide with alkyne. , 2009, Chemical communications.

[28]  T. Wirth,et al.  Fast synthesis of benzofluorenes by selenium-mediated carbocyclizations. , 2009, Angewandte Chemie.

[29]  Zhao‐Jing Zheng,et al.  PtCl2-catalyzed tandem triple migration reaction toward (Z)-1,5-dien-2-yl esters. , 2008, Organic letters.

[30]  D. Jung,et al.  Rhodium-catalyzed tandem conjugate addition-Mannich cyclization reaction: straightforward access to fully substituted tetrahydroquinolines. , 2008, The Journal of organic chemistry.

[31]  Xin Li,et al.  DFT study of the mechanisms of in water Au(I)-catalyzed tandem [3,3]-rearrangement/Nazarov reaction/[1,2]-hydrogen shift of enynyl acetates: a proton-transport catalysis strategy in the water-catalyzed [1,2]-hydrogen shift. , 2007, Journal of the American Chemical Society.

[32]  M. Murakami,et al.  Formation of carbocycles through sequential carborhodation triggered by addition of organoborons. , 2007, Chemical communications.

[33]  S. Suzen.  Antioxidant Activities of Synthetic Indole Derivatives and Possible Activity Mechanisms , 2007 .

[34]  Kenneth D Anderson,et al.  Design and synthesis of novel isoquinoline-3-nitriles as orally bioavailable Kv1.5 antagonists for the treatment of atrial fibrillation. , 2006, Journal of medicinal chemistry.

[35]  K. Kohn,et al.  A novel norindenoisoquinoline structure reveals a common interfacial inhibitor paradigm for ternary trapping of the topoisomerase I-DNA covalent complex , 2006, Molecular Cancer Therapeutics.

[36]  Jun‐An Ma,et al.  Catalytic asymmetric tandem transformations triggered by conjugate additions. , 2006, Angewandte Chemie.

[37]  G. Mugesh,et al.  Glutathione peroxidase (GPx)-like antioxidant activity of the organoselenium drug ebselen: unexpected complications with thiol exchange reactions. , 2005, Journal of the American Chemical Society.

[38]  Y. Nishibayashi,et al.  Asymmetric carboselenenylation reaction of alkenes with aromatic compounds. , 2005, Angewandte Chemie.

[39]  N. Urakawa,et al.  Inhibitory mechanism of papaverine on carbachol-induced contraction in bovine trachea. , 2005, Journal of pharmacological sciences.

[40]  J. Rocha,et al.  Organoselenium and organotellurium compounds: toxicology and pharmacology. , 2004, Chemical reviews.

[41]  J. Montgomery.  Nickel-catalyzed reductive cyclizations and couplings. , 2004, Angewandte Chemie.

[42]  Alexander Deiters,et al.  Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis. , 2004, Chemical reviews.

[43]  P. Hanson,et al.  Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis. , 2004, Chemical reviews.

[44]  M. Krische,et al.  Copper-catalyzed tandem conjugate addition-electrophilic trapping: ketones, esters, and nitriles as terminal electrophiles. , 2004, Journal of the American Chemical Society.

[45]  I. Beletskaya,et al.  Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes. , 2004, Chemical reviews.

[46]  T. Wirth,et al.  Selenocyclizations: control by coordination and by the counterion. , 2004, Angewandte Chemie.

[47]  Claus Jacob,et al.  Sulfur and selenium: the role of oxidation state in protein structure and function. , 2003, Angewandte Chemie.

[48]  J. Montgomery,et al.  A new catalytic conjugate addition/aldol strategy that avoids preformed metalated nucleophiles. , 2003, Journal of the American Chemical Society.

[49]  Chuo Chen,et al.  Synthesis of (+)-CP-263,114 [20] , 2000 .

[50]  M. Parnham,et al.  Ebselen: prospective therapy for cerebral ischaemia , 2000, Expert opinion on investigational drugs.

[51]  Reddy,et al.  A new 1,2-dihydroisoquinoline from the sponge petrosia similis , 1999, Journal of natural products.

[52]  R. Grigg,et al.  Palladium catalysed cascade cyclisation-anion capture, relay switches and molecular queues ☆ , 1999 .

[53]  G. Molander,et al.  Sequenced Reactions with Samarium(II) Iodide. Tandem Nucleophilic Acyl Substitution/Ketyl−Olefin Coupling Reactions , 1996 .

[54]  C. Copéret,et al.  Cyclic Carbopalladation. A Versatile Synthetic Methodology for the Construction of Cyclic Organic Compounds. , 1996, Chemical reviews.

[55]  S. Schreiber,et al.  Transannular Diels-Alder route to systems related to dynemicin A , 1990 .

[56]  H. Reich,et al.  Organoselenium chemistry. Redox chemistry of selenocysteine model systems , 1987 .

[57]  E. Cadenas,et al.  A novel biologically active seleno-organic compound--I. Glutathione peroxidase-like activity in vitro and antioxidant capacity of PZ 51 (Ebselen). , 1984, Biochemical pharmacology.

[58]  W. Parr.  Synthesis of selenium-containing para-phenylenediamines: novel antidegradants for natural rubber , 1982 .