Microwave‐Assisted Facile Synthesis of Furo[3,2‐b]indole Derivatives via Silver(I)‐Mediated [3+2] Cycloaddition

A robust one-pot process has been developed for the synthesis of a variety of furo[3,2-b]indoles from readily available o-propargylaminoacetophenones via silver(I)-mediated [3+2] cycloaddition.

[1]  S. Elliott,et al.  Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones. , 2010, Journal of the American Chemical Society.

[2]  V. Marathias,et al.  Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan. , 2010, Journal of the American Chemical Society.

[3]  Q. Zhang,et al.  Ag-containing all-carbon 1,3-dipoles: generation and formal cycloaddition for furo[3,2-b]-beta/gamma-lactams. , 2010, Chemical communications.

[4]  O. Kwon,et al.  Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines. , 2009, Journal of the American Chemical Society.

[5]  C. Sabot,et al.  Expeditious total syntheses of natural allenic products via aromatic ring umpolung. , 2008, Organic letters.

[6]  Liming Zhang,et al.  Au-containing all-carbon 1,3-dipoles: generation and [3+2] cycloaddition reactions. , 2008, Journal of the American Chemical Society.

[7]  C. Sabot,et al.  Intriguing formal [2+3] cycloaddition promoted by a hypervalent iodine reagent , 2008 .

[8]  M. Kimura,et al.  Convenient synthesis of pyrrolidines by amphiphilic allylation of imines with 2-methylenepropane-1,3-diols. , 2008, Angewandte Chemie.

[9]  L. Stanley,et al.  Enantioselective copper-catalyzed 1,3-dipolar cycloadditions. , 2008, Chemical reviews.

[10]  A. Padwa,et al.  The Rhodium(II) Carbenoid Cyclization-Cycloaddition Cascade of alpha-Diazo Dihydroindolinones for the Synthesis of Novel Azapolycyclic Ring Systems. , 2008, Tetrahedron.

[11]  S. Kirsch,et al.  Direct carbocyclization of aldehydes with alkynes: combining gold catalysis with aminocatalysis. , 2008, Organic letters.

[12]  V. Nair,et al.  Intramolecular 1,3-dipolar cycloaddition reactions in targeted syntheses , 2007 .

[13]  Q. Zhang,et al.  One-step synthesis of the tricyclic core of martinellic acid from 2-(cyanomethyl)-3-oxo-N-arylbutanamides. , 2007, The Journal of organic chemistry.

[14]  K. Muñiz Advancing palladium-catalyzed C-N bond formation: bisindoline construction from successive amide transfer to internal alkenes. , 2007, Journal of the American Chemical Society.

[15]  M. Pudlo,et al.  First Suzuki-Miyaura type cross-coupling of ortho-azidobromobenzene with arylboronic acids and its application to the synthesis of fused aromatic indole-heterocycles , 2007 .

[16]  Qun Liu,et al.  A Divergent Synthesis of γ-Iminolactones, Dihydroquinolin-2-ones, and γ-Lactames from β-Hydroxymethylcyclopropanylamides , 2007 .

[17]  Q. Zhang,et al.  A new efficient synthesis of pyranoquinolines from 1-acetyl N-aryl cyclopentanecarboxamides. , 2007, Organic letters.

[18]  Liming Zhang,et al.  Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center. , 2007, Journal of the American Chemical Society.

[19]  H. Pellissier Asymmetric 1,3-Dipolar Cycloadditions , 2007 .

[20]  Q. Zhang,et al.  Domino ring-opening/recyclization reactions of doubly activated cyclopropanes as a strategy for the synthesis of furoquinoline derivatives. , 2007, Angewandte Chemie.

[21]  S. Danishefsky,et al.  On the rearrangement of an azaspiroindolenine to a precursor to phalarine: mechanistic insights. , 2007, Angewandte Chemie.

[22]  S. Danishefsky,et al.  Total synthesis of phalarine. , 2007, Angewandte Chemie.

[23]  V. Snieckus,et al.  Asymmetric total synthesis of (-)-panacene and correction of its relative configuration. , 2006, Organic letters.

[24]  Chul-Seung Park,et al.  Electrophysiological Characterization of Benzofuroindole-Induced Potentiation of Large-Conductance Ca2+-Activated K+ Channels , 2006, Molecular Pharmacology.

[25]  R. Wójcik,et al.  10b-Substituted hexahydropyrrolo-isoquinolines: studies on diastereoselective formation of a quaternary carbon stereocenter via N-acyliminium ion cyclization , 2006 .

[26]  P. Pohlhaus,et al.  Enantiospecific Sn(II)- and Sn(IV)-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes. , 2005, Journal of the American Chemical Society.

[27]  Chia Hui Lin,et al.  Manganese(III) Acetate Mediated Oxidative Free Radical Reactions between Indole Derivatives and 1,3-Dicarbonyl Compounds , 2005 .

[28]  L. Hurley,et al.  Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones. , 2005, Journal of medicinal chemistry.

[29]  W. Roush,et al.  Nucleophilic Phosphine Organocatalysis , 2004 .

[30]  V. Yadav,et al.  Formal [3+2] addition of acceptor-substituted cyclopropylmethylsilanes with aryl acetylenes. , 2004, Angewandte Chemie.

[31]  Tetsuro Ito,et al.  Regioselective Oxidative Coupling of 4-Hydroxystilbenes: Synthesis of Resveratrol and ε-Viniferin (E)-Dehydrodimers , 2004 .

[32]  M. Krische,et al.  Intramolecular organocatalytic [3+2] dipolar cycloaddition: stereospecific cycloaddition and the total synthesis of (+/-)-hirsutene. , 2003, Angewandte Chemie.

[33]  M. Krische,et al.  Catalytic diastereoselective synthesis of diquinanes from acyclic precursors. , 2003, Journal of the American Chemical Society.

[34]  S. Kanemasa Metal-Assisted Stereocontrol of 1,3-Dipolar Cycloaddition Reactions , 2002 .

[35]  S. Antane,et al.  Synthesis and potassium channel opening activity of substituted 10H-benzo[4,5]furo[3,2-b]indole-and 5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acids. , 2001, Bioorganic & medicinal chemistry letters.

[36]  W. H. Pearson,et al.  Total synthesis of the Kopsia lapidilecta alkaloid (+/-)-lapidilectine B. , 2001, Journal of the American Chemical Society.

[37]  X. Lu,et al.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis. , 2001, Accounts of chemical research.

[38]  I. Namboothiri,et al.  Stereoselective Intramolecular 1,3-Dipolar Cycloadditions , 2001 .

[39]  K. Gothelf,et al.  Asymmetric 1,3-Dipolar Cycloaddition Reactions. , 1998, Chemical reviews.

[40]  M. Lautens,et al.  Transition Metal-Mediated Cycloaddition Reactions. , 1996, Chemical reviews.

[41]  C. Masse,et al.  Diastereoselective Reactions of Chiral Allyl and Allenyl Silanes with Activated C:X .pi.-Bonds , 1995 .

[42]  K. Kawasaki,et al.  Directing Effect of 1,3-Dimethylimidazolidine in Ortho Lithiation Changes with Its Vicinal Group , 1994 .

[43]  K. Suwanborirux,et al.  Xanthones and vismiones from Psorospermum febrifugum , 1993 .

[44]  M. Welker 3 + 2 Cycloaddition reactions of transition-metal 2-alkynyl and .eta.1-allyl complexes and their utilization in five-membered-ring compound syntheses , 1992 .

[45]  K. Nicholas,et al.  Cobalt-mediated Alkylation of Siloxy Furans , 1991 .

[46]  M. Brimble,et al.  Synthesis of 5-epi-7-deoxykalafungin and 5-epi-7-O-methylkalafungin , 1990 .

[47]  D. Burg,et al.  An anionic 3 + 2 cyclization-elimination route to cyclopentenes , 1989 .

[48]  K. Suwanborirux,et al.  Novel tetrahydrofurobenzofuranoxanthones from psorospermum febrifugum , 1989 .

[49]  J. J. Gibson,et al.  Synthesis of the cis-3a,8b-dihydrofuro[3,2-b]benzofuran-2(3H)-one ring system via a furofuran annulation to activated benzoquinones , 1989 .

[50]  M. C. Conroy,et al.  Inhibition of Human Neutrophil Activation by the Allergic Mediator Release Inhibitor, CI‐922: Differential Inhibition of Responses to a Variety of Stimuli , 1987, Journal of leukocyte biology.

[51]  H. Wagner,et al.  Synthese von Americanin‐D , 1987 .

[52]  S. Okuyama,et al.  Furo[3,2-b]indole derivatives. V. Synthesis and structure-activity studies of 4-substituted 2-(4-methylpiperazinylcarbonyl)-6-trifluoromethylfuro[3,2- b]indole derivatives with analgesic and antiinflammatory activities. , 1987, Chemical & pharmaceutical bulletin.

[53]  J. J. Gibson,et al.  1,4-Addition of 2-trimethylsilyloxyfuran to quinones: a facile route to the furo[3,2-b]benzofuran nucleus , 1987 .

[54]  L. Robichaud,et al.  CI-922--a novel, potent antiallergic compound--II. Activity in animal models of allergy. , 1987, International journal of immunopharmacology.

[55]  L. Robichaud,et al.  CI-922--a novel, potent antiallergic compound--I. Inhibition of mediator release in vitro. , 1987, International journal of immunopharmacology.

[56]  S. Okuyama,et al.  Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities. , 1986, Journal of medicinal chemistry.

[57]  S. Okuyama,et al.  Furo[3,2-b]indole derivatives. III. Structure-activity studies of 4,6-disubstituted N-(3-piperidinopropyl)furo[3,2-b]indole-2-carboxamide derivatives for analgesic and antiinflammatory activities. , 1986, Chemical & pharmaceutical bulletin.

[58]  B. Trost [3+2] Cycloaddition Approaches to Five‐Membered Rings via Trimethylenemethane and Its Equivalents [New Synthetic Methods (55)] , 1986 .

[59]  B. Trost Fünfgliedrige Ringe durch [3+2]-Cycloaddition mit Trimethylenmethan und Syntheseäquivalenten , 1986 .

[60]  S. Okuyama,et al.  Pharmacological studies of furo [3,2-b]indole derivatives. II. Analgesic effect of FI-302, N-(3-piperidinopropyl)-4-methyl-6-trifluoromethyl-furo[3,2-b]ind ole-2-carboxamide, in experimental animals. , 1985, Journal of pharmacobio-dynamics.

[61]  S. Okuyama,et al.  Pharmacological studies of furo [3,2-b] indole derivatives. I. Analgesic, anti-pyretic and anti-inflammatory effects of FI-302, N-(3-piperidinopropyl)-4-methyl-6-trifluoromethyl-furo [3,2-b]indole-2-carboxamide, in experimental animals. , 1985, Journal of pharmacobio-dynamics.

[62]  Z. Yoshida,et al.  Palladium catalyzed oxycarbonylation of 4-penten-1,3-diols: efficient stereoselective synthesis of cis 3-hydroxytetrahydrofuran 2-acetic acid lactones , 1985 .

[63]  P. Unangst,et al.  Acidic furo[3,2-b]indoles. A new series of potent antiallergy agents. , 1984, Journal of medicinal chemistry.

[64]  P. Unangst,et al.  Indole esters as heterocyclic synthons. III. Preparation and reactions of furo[3,2‐b]indoles , 1984 .

[65]  M. Semmelhack,et al.  Direct synthesis of pyran-lactones related to naphthoquinoneantibiotics , 1984 .

[66]  A. Basak,et al.  Scope and stereochemical course of the (trimethylsilyl)cyclopentene annulation , 1983 .

[67]  Ken S. Feldman,et al.  (±)-パナセンの全合成 | 文献情報 | J-GLOBAL 科学技術総合リンクセンター , 1982 .

[68]  K. S. Feldman Biomimetic synthesis of (±) panacene , 1982 .

[69]  A. Tanaka,et al.  Synthesis of 4H-furo[3,2-b]indole derivatives. III. Preparation of 4H-furo[3,2-b]indole-2-carboxylic acid derivatives† , 1979 .

[70]  A. Tanaka,et al.  Synthesis of 4H‐furo[3,2‐b]indoles. II. Bromination, acylation and nitration of 4H‐ and 4‐benzoylfuro[3,2‐b]indoles , 1978 .

[71]  A. Tanaka,et al.  Synthesis of 4H‐furo[3,2‐b]indole derivatives A new heterocyclic ring system , 1977 .

[72]  T. Eisner,et al.  Panacene: An aromatic bromoallene from a sea hare (Aplysia brasiliana) , 1977 .

[73]  E. Warnhoff,et al.  On the oxidative dimerization of 2,3-dialkylindoles , 1976 .

[74]  T. Saegusa,et al.  Synthesis of 1,4-diketones by the reaction of silyl enol ether with silver oxide. Regiospecific formation of silver(I) enolate intermediates , 1975 .

[75]  G. Whitesides,et al.  Preparation and thermal decomposition of n-alkyl(tri-n-butylphosphine)silver(I) reagents , 1974 .

[76]  S. Mclean,et al.  Autoxidation of 2,3-Dialkylindoles , 1971 .

[77]  E. Warnhoff,et al.  Indole Oxidation : the Dimer of 3-Hydroxy-2,3-dimethylindolenine' , 1971 .

[78]  E. Nannipieri,et al.  A dimeric autoxidation product of 2,3-dimethylindole , 1969 .

[79]  D. Curtin,et al.  Stereochemistry and Reactions with Hydroxyl Ion and with Silver Oxide of the 2-Bromo-4-phenylcyclohexanols and the 1-Methyl-2-bromo-4-phenylcyclohexanols1 , 1960 .