Selective Synthesis of 2-Indolyl-3-oxoindolines or 2-(2-Aminophenyl)quinolines through Cu(II)- or Bi(III)-Catalyzed Tunable Dimerizations of 2-Alkynylanilines.

A novel and selective synthesis of 2-indolyl-3-oxoindolines or 2-(2-aminophenyl)quinolines through tunable dimerizations of 2-alkynylanilines is presented. Mechanistically, the formation of 2-indolyl-3-oxoindolines involves a Cu(OAc)2/O2-promoted intramolecular cyclization of 2-alkynylaniline to give the required indole and 3H-indol-3-one intermediates followed by the indolylation of 3H-indol-3-one. On the other hand, the formation of 2-(2-aminophenyl)quinolines is believed to go through a Bi(OTf)3/MesCO2H-catalyzed intermolecular N-nucleophilic addition between two 2-alkynylaniline molecules to give an enamine intermediate followed by its intramolecular C-nucleophilic addition/annulation. Notable features of these new methods include easily obtainable substrates, economical catalysts and oxidant, controllable selectivity, and high versatility toward diverse products.

[1]  Yong‐Min Liang,et al.  Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans. , 2020, The Journal of organic chemistry.

[2]  J. Tepe,et al.  Sc(OTf)3 mediated one pot synthesis of 2,3-disubstituted quinolines from anilines and epoxides. , 2020, The Journal of organic chemistry.

[3]  Kundi Yang,et al.  Rhodium(III)-Catalyzed Oxidative Annulation of 4-Aminoquinolines and Acrylate through Two Consecutive C(sp2)-H Activations. , 2020, Organic letters.

[4]  Hua Zhang,et al.  Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones , 2020, Molecules.

[5]  Xuesen Fan,et al.  Complementary C-H Functionalization Mode of Benzoylacetonitriles: Computer-Augmented Study of a Regio- and Stereoselective Synthesis of Functionalized Benzofulvenes. , 2019, Organic letters.

[6]  Liang‐Hua Zou,et al.  Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives. , 2019, The Journal of organic chemistry.

[7]  Xuesen Fan,et al.  Two birds with one stone: one-pot simultaneous synthesis of 2,2,2-trifluoroethylphenanthridines and benzochromenones featuring the utilization of the byproduct of Togni's reagent , 2019, Green Chemistry.

[8]  Bin Li,et al.  Synthesis of Fused or Spiro Polyheterocyclic Compounds via the Dehydrogenative Annulation Reactions of 2-Arylindazoles with Maleimides. , 2019, Organic letters.

[9]  Indresh Kumar,et al.  Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative dimerization of 2-aryl indoles and cross-addition with indoles , 2019, RSC advances.

[10]  Lianhui Wang,et al.  Rh(III)-Catalyzed Sequential C-H Amination/Annulation Cascade Reactions: Synthesis of Multisubstituted Benzimidazoles. , 2019, Organic letters.

[11]  T. Lu,et al.  Asymmetric Synthesis of C2-Quaternary Indolin-3-ones Enabled by N-Heterocyclic Carbene Catalysis. , 2019, Organic letters.

[12]  Xuesen Fan,et al.  Tunable Synthesis of Indolo[3,2- c]quinolines or 3-(2-Aminophenyl)quinolines via Aerobic/Anaerobic Dimerization of 2-Alkynylanilines. , 2019, Organic letters.

[13]  Q. Ma,et al.  RuII-Catalyzed/NH2-Assisted Selective Alkenyl C-H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines. , 2019, Organic letters.

[14]  Changjin Zhu,et al.  Axially Chiral Cyclic Phosphoric Acid Enabled Enantioselective Sequential Additions. , 2019, Organic letters.

[15]  Cheng Peng,et al.  Recent advances in the synthesis of C2-spiropseudoindoxyls. , 2019, Organic & biomolecular chemistry.

[16]  W. Su,et al.  Metal-free synthesis of 2,2-disubstituted indolin-3-ones. , 2019, Organic & biomolecular chemistry.

[17]  T. Bein,et al.  Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines , 2018, Journal of the American Chemical Society.

[18]  Weidong Rao,et al.  Pd-Catalyzed One-Pot Two-Step Synthesis of 2-(1H -indol-3-yl)-2-phenylindolin-3-ones from 2-Alkynyl Arylazides and Indoles , 2018, ChemistrySelect.

[19]  H. Morita,et al.  Bisleuconothines B-D, Modified Eburnane-Aspidosperma Bisindole Alkaloids from Leuconotis griffithii. , 2018, Journal of natural products.

[20]  C. Oh,et al.  Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to p-quinone methides: efficient access to unsymmetrical diarylindolylmethanes , 2018 .

[21]  V. Vasantha,et al.  Rh-Catalyzed regioselective C–H activation and C–C bond formation: synthesis and photophysical studies of indazolo[2,3-a]quinolines , 2018 .

[22]  Xuesen Fan,et al.  One‐Pot Synthesis of Fused N,O‐Heterocycles through Rh(III)‐Catalyzed Cascade Reactions of Aromatic/Vinylic N‐Alkoxy‐ Amides with 4‐Hydroxy‐2‐Alkynoates , 2018 .

[23]  B. Sridhar,et al.  Oxidative Asymmetric Aza-Friedel-Crafts Alkylation of Indoles with 3-Indolinone-2-carboxylates Catalyzed by a BINOL Phosphoric Acid and Promoted by DDQ. , 2018, Chemistry, an Asian journal.

[24]  David J. Marchant,et al.  Dual Catalytic Synthesis of Antiviral Compounds Based on Metallocarbene-Azide Cascade Chemistry. , 2018, The Journal of organic chemistry.

[25]  Dan Yang,et al.  Ruthenium-Catalyzed Oxidative Dearomatization of Indoles for the Construction of C2-Quaternary Indolin-3-ones , 2018, Synlett.

[26]  Q. Song,et al.  Copper-Catalyzed Radical Difluoroalkylation and Redox Annulation of Nitroalkynes for the Construction of C2-Tetrasubstituted Indolin-3-ones. , 2018, Organic letters.

[27]  Jun‐An Ma,et al.  Catalytic Asymmetric Mukaiyama-Mannich Reaction of Cyclic C-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones. , 2017, Organic letters.

[28]  Xuesen Fan,et al.  Synthesis of 3-acylquinolines through Cu-catalyzed double C(sp3)–H bond functionalization of saturated ketones , 2017 .

[29]  L. Zu,et al.  Total Synthesis of (±)-Grandilodine B. , 2017, Organic letters.

[30]  Chunhua Liu,et al.  Gold/Copper-Co-catalyzed Tandem Reactions of 2-Alkynylanilines: A Synthetic Strategy for the C2-Quaternary Indolin-3-ones. , 2017, Organic letters.

[31]  Dongnai Ye,et al.  A multifunctionalized strategy of indoles to C2-quaternary indolin-3-ones via a TEMPO/Pd-catalyzed cascade process. , 2017, Organic & biomolecular chemistry.

[32]  Wen‐Hua Sun,et al.  Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(II): synthesis, characterization and catalytic performance in Heck coupling , 2016 .

[33]  K. Amsharov,et al.  Aluminium-mediated aromatic C-F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks. , 2016, Chemical communications.

[34]  Chenhao Zhang,et al.  Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch , 2016 .

[35]  Xiuling Cui,et al.  Access to C4-Functionalized Quinolines via Copper-Catalyzed Tandem Annulation of Alkynyl Imines with Diazo Compounds. , 2016, The Journal of organic chemistry.

[36]  S. K. Guchhait,et al.  Oxidative Dearomatization of Indoles via Pd-Catalyzed C-H Oxygenation: An Entry to C2-Quaternary Indolin-3-ones. , 2016 .

[37]  P. Perumal,et al.  Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines , 2016 .

[38]  Jian-rong Gao,et al.  Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters. , 2015, Angewandte Chemie.

[39]  K. Lee,et al.  Indole alkaloid glycosides from the aerial parts of Strobilanthes cusia. , 2014, Journal of natural products.

[40]  Y. Mu,et al.  Facile synthesis of acridine derivatives by ZnCl2-promoted intramolecular cyclization of o-arylaminophenyl Schiff bases. , 2014, Organic letters.

[41]  C. Ramana,et al.  Synthesis of pseudo-indoxyl derivatives via sequential Cu-catalyzed S(N)Ar and Smalley cyclization. , 2013, Chemical communications.

[42]  V. Puranik,et al.  InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisine A. , 2012, Chemistry.

[43]  Jae Hong Lee,et al.  Synthesis of a new fluorescent small molecule probe and its use for in vivo lipid imaging. , 2011, Chemical communications.

[44]  L. McElwee‐White,et al.  Dimerization of ethynylaniline to a quinoline derivative using a ruthenium/gold heterobimetallic catalyst , 2010 .

[45]  P. Perumal,et al.  Gold(III) Chloride CatalyzedIntermolecular Dimerization of 2-Ethynylanilines: Synthesisof Substituted Quinolines , 2009 .

[46]  Pauline N. Wyrembak,et al.  Alkyne-linked 2,2-disubstituted-indolin-3-one oligomers as extended beta-strand mimetics. , 2009, Journal of the American Chemical Society.

[47]  M. Akazome,et al.  Synthesis and physical properties of various organic dyes derived from a single core skeleton, 1,2-dihydroindol-3-one , 2009 .

[48]  T. Konakahara,et al.  InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group. , 2008, The Journal of organic chemistry.

[49]  Ji-Jun Chen,et al.  Isatisine A, a novel alkaloid with an unprecedented skeleton from leaves of Isatis indigotica. , 2007, Organic letters.

[50]  M. Stevens,et al.  Synthetic strategies to a telomere-targeted pentacyclic heteroaromatic salt. , 2007, Organic & biomolecular chemistry.

[51]  Chen-Wei Jao,et al.  Indole alkaloids from Cephalanceropsis gracilis. , 2006, Journal of natural products.

[52]  T. Konakahara,et al.  Direct synthesis of polysubstituted quinoline derivatives by InBr3-promoted dimerization of 2-ethynylaniline derivatives. , 2006, The Journal of organic chemistry.

[53]  W. Mcwhorter,et al.  Synthesis of 8-desbromohinckdentine A1. , 2003, Journal of the American Chemical Society.