Indium-Mediated Intramolecular Reaction of N-(2-Iodobenzoyl)azabenzonorbornadienes: A General Access to Dihydrobenzo[c]phenanthridinones.

An efficient synthesis of dihydrobenzo[c]phenanthridinones was achieved by utilizing an indium(0)-mediated intramolecular cyclization reaction under ligand- and base-free conditions. A variety of functional groups were tolerated in the present protocol.

[1]  Jen-Chieh Hsieh,et al.  Copper-Catalyzed Annulation: A Method for the Systematic Synthesis of Phenanthridinium Bromide. , 2016, Organic letters.

[2]  David A Petrone,et al.  Additive effects in the palladium-catalyzed carboiodination of chiral N-allyl carboxamides. , 2014, Angewandte Chemie.

[3]  Xiaohua Xu,et al.  Diastereoselection during 1,2-addition of 3-bromomethyl-5H-furan-2-one to α-chiral aldehydes mediated by indium in aqueous and organic solvent systems: direct route to obtain optically active α-methylene-γ-butyrolactones , 2014 .

[4]  Xiaohua Xu,et al.  Enantioselective Palladium‐Catalyzed Ring‐Opening Reaction of Azabenzonorbornadienes with Methyl 2‐Iodobenzoate: An Efficient Access to cis‐Dihydrobenzo[c]phenanthridinones , 2013 .

[5]  Ying Liang,et al.  Ligand-free indium(III)-catalyzed Heck reaction , 2013 .

[6]  Xiaohua Xu,et al.  Palladium-catalyzed annulation reactions of methyl o-halobenzoates with azabicyclic alkenes: a general protocol for the construction of benzo[c]phenanthridine derivatives , 2013 .

[7]  M. Sauvain,et al.  Short synthesis and antimalarial activity of fagaronine. , 2012, Bioorganic & Medicinal Chemistry.

[8]  Xiaohua Xu,et al.  Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone. , 2012, Organic & biomolecular chemistry.

[9]  Xiaohua Xu,et al.  Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: application to the total synthesis of benzo[c]phenanthridine alkaloids. , 2011, Organic & biomolecular chemistry.

[10]  M. Lautens,et al.  Formal synthesis of nitidine and NK109 via palladium-catalyzed domino direct arylation/N-arylation of aryl triflates. , 2011, Organic letters.

[11]  Jubi John,et al.  Palladium catalyzed ring opening of azabicyclic olefins with organoindium and gallium reagents: a facile access towards benzylated cyclopentanoids , 2010 .

[12]  V. Papoian,et al.  Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal. , 2008, The Journal of organic chemistry.

[13]  M. Lautens,et al.  Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy. , 2008, Chemistry.

[14]  J. Baltaze,et al.  Direct C-glycosylation by indium-mediated alkynylation on sugar anomeric position. , 2008, Organic letters.

[15]  Jubi John,et al.  Palladium-catalyzed ring opening of azabicyclic olefins with organoindium reagents : a simple, clean, and efficient synthesis of functionalized cyclopentenes , 2007 .

[16]  F. Huguenot,et al.  Ferrier-type alkynylation reaction mediated by indium. , 2007, Organic letters.

[17]  J. Uziel,et al.  Recent Advances in Indium-Promoted Organic Reactions , 2007 .

[18]  M. Lautens,et al.  Enantioselective total synthesis of (+)-homochelidonine by a PdII-catalyzed asymmetric ring-opening reaction of a meso-azabicyclic alkene with an aryl boronic acid. , 2007, Angewandte Chemie.

[19]  J. Uziel,et al.  Gram-Scale Preparation of a p-(C-Glucopyranosyl)-L-phenylalanine Derivative by a Negishi Cross-Coupling Reaction , 2006 .

[20]  G. Koh,et al.  Suppression of angiogenesis by the plant alkaloid, sanguinarine. , 2004, Biochemical and biophysical research communications.

[21]  V. Nair,et al.  Indium- and gallium-mediated carbon-carbon bond-forming reactions in organic synthesis , 2004 .

[22]  E. LaVoie,et al.  2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents. , 2003, Bioorganic & medicinal chemistry.

[23]  Nadège Lubin-Germain,et al.  Indium-mediated formation of propargyl ketones from aldehydes or acyl chlorides , 2003 .

[24]  M. Lautens,et al.  An expedient enantioselective route to diaminotetralins: application in the preparation of analgesic compounds. , 2002, Organic letters.

[25]  G. Grynkiewicz,et al.  Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives. , 2001, European journal of medicinal chemistry.

[26]  B. Ranu Indium Metal and Its Halides in Organic Synthesis , 2000 .

[27]  T. Ishikawa,et al.  Recent Advances on Antitumor-Active Benzo[c]phenanthridine Alkaloids , 1999 .

[28]  Chien‐Hong Cheng,et al.  Palladium-Catalyzed Reductive Couplings of Organic Halides with 7-Heteroatom Norbornadienes. New Synthetic Methods for Substituted Aryls and cis-1,2-Dihydro-1-naphthyl Alcohols and Carbamates , 1995 .

[29]  D. J. Moore,et al.  A clinical comparison of antibacterial mouthrinses: effects of chlorhexidine, phenolics, and sanguinarine on dental plaque and gingivitis. , 1989, Journal of periodontology.

[30]  M. Shamma,et al.  The benzophenanthridine alkaloids , 1984 .

[31]  I. Ernest,et al.  Neurotrope und psychotrope Substanzen XXII. Weitere Chlorderivate des 10-(4-Methylpiperazino)-10,11-dihydrodibenzo[ b,f ]thiepins und einige verwandte Stoffe , 1968 .