Iodine-mediated intramolecular amination of ketones: the synthesis of 2-acylindoles and 2-acylindolines by tuning N-protecting groups.

A general method for constructing both 2-acylindoles and 2-acylindolines via I2-mediated intramolecular C-N bond formation is presented, and the selective formation of either 2-acylindoles or 2-acylindolines just depends on the nitrogen protecting groups used in the same substrate skeletons.

[1]  B. Sridhar,et al.  Cu(OTf)2-catalyzed synthesis of 2,3-disubstituted indoles and 2,4,5-trisubstituted pyrroles from α-diazoketones. , 2013, Organic letters.

[2]  W. Xiao,et al.  Synthesis of indoles through highly efficient cascade reactions of sulfur ylides and N-(ortho-chloromethyl)aryl amides. , 2012, Angewandte Chemie.

[3]  Q. Zou,et al.  Calophyline A, a new rearranged monoterpenoid indole alkaloid from Winchia calophylla. , 2012, Organic letters.

[4]  M. Zeller,et al.  Synthesis, antimicrobial, antimycobacterial and structure-activity relationship of substituted pyrazolo-, isoxazolo-, pyrimido- and mercaptopyrimidocyclohepta[b]indoles. , 2012, European journal of medicinal chemistry.

[5]  L. Bohn,et al.  Synthesis of conolidine, a potent non-opioid analgesic for tonic and persistent pain. , 2011, Nature chemistry.

[6]  H. Alper,et al.  Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of 2-nitrovinylarenes. , 2011, The Journal of organic chemistry.

[7]  J. Lavrado,et al.  Indoloquinolines as scaffolds for drug discovery. , 2010, Current medicinal chemistry.

[8]  J. Florent,et al.  Palladium-catalyzed domino C,N-coupling/carbonylation/Suzuki coupling reaction: an efficient synthesis of 2-aroyl-/heteroaroylindoles. , 2009, Organic letters.

[9]  J. Qu,et al.  Boiling water-catalyzed neutral and selective N-Boc deprotection. , 2009, Chemical communications.

[10]  Giuseppe Cremonesi,et al.  Heterocycles from Ylides. Part X. Synthesis of 3-Hydroxy-2,3-dihydroindoles by a Domino Reaction , 2007 .

[11]  J. Bonjoch,et al.  Synthetic studies about strychnopivotine: synthesis of the bridged azatricyclic fragment , 2007 .

[12]  Jaime. Escribano,et al.  Dioxomolybdenum(VI)‐Catalyzed Reductive Cyclization of Nitroaromatics. Synthesis of Carbazoles and Indoles , 2007 .

[13]  Andrea Brancale,et al.  Indole, a core nucleus for potent inhibitors of tubulin polymerization , 2007, Medicinal research reviews.

[14]  A. Padwa,et al.  Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade. , 2007, Organic letters.

[15]  Giuseppe Cremonesi,et al.  Synthesis of 2-hydroxy-1,2,3,4-tetrahydroquinoline derivatives by a cyclocondensation reaction , 2006 .

[16]  S. Minakata,et al.  Practical and convenient synthesis of N-heterocycles: stereoselective cyclization of N-alkenylamides with t-BuOI under neutral conditions. , 2006, Organic letters.

[17]  B. Flynn,et al.  Selective endo and exo iodocyclizations in the synthesis of quinolines and indoles. , 2006, Organic letters.

[18]  Giuseppe Cremonesi,et al.  Heterocycles from ylides. Part IX. A convenient synthesis of 1-sulfonyl-2,3-disubstituted 2,3-dihydroindoles , 2005 .

[19]  H. Kogen,et al.  Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: application to the total syntheses of benzastatin E and natural virantmycin , 2005 .

[20]  T. Beckers,et al.  Bis(1H-2-indolyl)methanones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase. , 2002, Journal of medicinal chemistry.

[21]  J. Yadav,et al.  Aromatization of Hantzsch 1,4-dihydropyridines with I 2 -MeOH , 2000 .

[22]  A. Padwa,et al.  A New Method for the Formation of Octahydroindole Alkaloids via the Intramolecular Diels−Alder Reaction of 2-Amidofurans , 1998 .

[23]  P. Imbach,et al.  Antihyperglycemic activities of cryptolepine analogues: an ethnobotanical lead structure isolated from Cryptolepis sanguinolenta. , 1998, Journal of medicinal chemistry.

[24]  M. Cooper,et al.  Indole-β-nucleophilic substitution. Part 9 nitrogen nucleophiles. Syntheses of hydroxycryptolepine, cryptolepine, and quindoline , 1996 .

[25]  T. Spitzer,et al.  Elucidation of the structure of quindolinone, a minor alkaloid of cryptolepis sanguinolenta: Submilligram 1H‐13c and 1H‐15N heteronuclear shift correlation experiments using micro inverse‐detection , 1995 .

[26]  Yoshihisa Watanabe,et al.  Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives , 1994 .

[27]  Yoshihisa Watanabe,et al.  Novel Synthesis of Indoles via Palladium-Catalyzed Reductive N-Heterocyclization of o-Nitrostyrene Derivatives , 1992 .

[28]  V. Snieckus,et al.  The N-tert-butylcarbamoyl directed metalation group for the regiospecific synthesis of 2-substituted pyrroles and indoles , 1991 .

[29]  F. G. Bordwell,et al.  Equilibrium Acidities in Dimethyl Sulfoxide Solution , 1988 .

[30]  A. Katritzky,et al.  Carbon Dioxide: A Reagent for the Protection of Nucleophilic Centres and the Simultaneous Activation of Alternative Locations to Electrophilic Attack. , 1986 .

[31]  G. Gribble,et al.  Generation and reactions of 3-lithio-1-(phenylsulfonyl)indole , 1982 .

[32]  J. Weber,et al.  Anellierte Chinoline, 6. Mitt. 10H‐Indolo[3,2‐b]chinoline , 1981 .

[33]  D. Black,et al.  A simple synthesis of 2-acyl indoles from isatins , 1980 .

[34]  R. Sundberg,et al.  Syntheses with N-protected 2-lithioindoles , 1973 .

[35]  Charles David Jones,et al.  Direct synthesis of 2-acylindoles , 1972 .

[36]  J. Joule,et al.  The syntheses of (±)-dasycarpidone, (±)-3-epi-dasycarpidone, (±)-uleine and (±)-3-epi-uleine , 1969 .

[37]  C. Djerassi,et al.  α-Iodoketones (Part 2).1 Reaction of Enol Acetates with N-Iodosuccinimide2 , 1953 .