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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Efficient and Straightforward Synthesis of Tetrahydrocarbazoles and 2,3-Dimethyl Indoles Catalyzed by CAN

P. Prabhakara Varma Department of Postgraduate Studies and Research in Industrial Chemistry and Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta, Karnataka, India
,
Bailure S. Sherigara Department of Postgraduate Studies and Research in Industrial Chemistry and Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta, Karnataka, India
,
Kittapa M. Mahadevan Department of Postgraduate Studies and Research in Industrial Chemistry and Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta, Karnataka, IndiaCorrespondence[email protected].
&
Vijaykumar Hulikal Bioorganics and Applied Materials, Bangalore, India
Pages 158-165 | Received 04 Apr 2008, Published online: 15 Feb 2011

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N. Anitha, B. Sudhakar Reddy, N.M. Sekhar, K. Venugopal Reddy & E.R. R. Chandrasekhar. (2014) Alternative Approach to Synthesis of 3-(4-chloro butyl)-1H-indole-5-carbonitrile: A Key Intermediate of Vilazodone Hydrochloride, an Antidepressant Drug. Synthetic Communications 44:24, pages 3563-3571.
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KittappaM. Mahadevan, HosanagaraN. Harishkumar, JagadeeshN. Masagalli & HosapalyaT. Srinivasa. (2013) Synthesis and Liquid Crystal Property of New Fluoro Coumarin Carboxylates. Molecular Crystals and Liquid Crystals 570:1, pages 20-35.
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Articles from other publishers (26)

Eagala Ramesh, Laxman D. Nandawadekar, Ramana Sreenivasa Rao & D. Srinivasa Reddy. (2023) Scalable Synthesis of Silacyclohexanones and Ready Access to Silicon Building Blocks. Organic Letters.
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Weijia Li, Juanjuan Wang, Weihai Fang, Liangliang Wu & Xuebo Chen. (2023) Co-function Mechanisms of Chlorine and Alkoxy Radicals in Cerium-Catalyzed C–H Functionalization of Alkane Mediated by Visible Light. The Journal of Physical Chemistry Letters 14:26, pages 6187-6192.
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Xia Chen & Xiao-Yu Zhou. (2022) Ruthenium-Catalyzed Regioselective Synthesis of C3-Alkylated Indoles Following Transfer Hydrogenation or Borrowing Hydrogen Strategy. Synthesis 55:09, pages 1460-1466.
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Xia Chen & Xiao-Yu Zhou. (2022) A Convenient, Efficient, and Inexpensive Copper(I) Complex Catalyzed Sonogashira Cross-Coupling of o-Iodoanilines with Terminal Alkynes. Synthesis 55:08, pages 1213-1220.
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Saira Banu, Shubham Choudhari, Girija Patel & Prem P. Yadav. (2021) Auto-tandem PET and EnT photocatalysis by crude chlorophyll under visible light towards the oxidative functionalization of indoles. Green Chemistry 23:8, pages 3039-3047.
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Yizhan Zhai, Shu-Li You & Shengming Ma. (2019) Palladium-catalyzed intermolecular allenylation reactions of 2,3-disubstituted indoles and allenyl carbonate. Organic & Biomolecular Chemistry 17:30, pages 7128-7130.
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Sarfaraz Ali Ghumro, Rima D. Alharthy, Mariya al-Rashida, Shakil Ahmed, Muhammad Imran Malik & Abdul Hameed. (2017) N-Alkylated 1,4-Diazabicyclo[2.2.2]octane–Polyethylene Glycol Melt as Deep Eutectic Solvent for the Synthesis of Fisher Indoles and 1 H -Tetrazoles . ACS Omega 2:6, pages 2891-2900.
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Chongqing Pan, Zixi Zhu, Mingkai Zhang & Zhenhua Gu. (2017) Palladium-Catalyzed Enantioselective Synthesis of 2-Aryl Cyclohex-2-enone Atropisomers: Platform Molecules for the Divergent Synthesis of Axially Chiral Biaryl Compounds. Angewandte Chemie International Edition 56:17, pages 4777-4781.
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Chongqing Pan, Zixi Zhu, Mingkai Zhang & Zhenhua Gu. (2017) Palladium‐Catalyzed Enantioselective Synthesis of 2‐Aryl Cyclohex‐2‐enone Atropisomers: Platform Molecules for the Divergent Synthesis of Axially Chiral Biaryl Compounds. Angewandte Chemie 129:17, pages 4855-4859.
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Amrutha P. Thankachan, Kallikkakam S. Sindhu, Sankuviruthiyil M. Ujwaldev & Gopinathan Anilkumar. (2017) Synthesis of substituted benzofurans and indoles by Zn-catalyzed tandem Sonogashira-cyclization strategy. Tetrahedron Letters 58:6, pages 536-540.
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Sarfaraz Ali Ghumro, Sana Saleem, Mariya al-Rashida, Nafees Iqbal, Rima D. Alharthy, Shakil Ahmed, Syed Tarique Moin & Abdul Hameed. (2017) N,N-Dimethylpyridin-4-amine (DMAP) based ionic liquids: evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1H-tetrazole synthesis. RSC Advances 7:54, pages 34197-34207.
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Gordon W. Gribble. 2016. Indole Ring Synthesis. Indole Ring Synthesis 41 115 .
Sridhar Madabhushi, Venkata Sairam Vangipuram, Kishore Kumar Reddy Mallu, Raveendra Jillella, Srinivas Kurva & Shanthan Rao Pamulaparthi. (2013) Ceric (IV) ammonium nitrate (CAN) mediated synthesis of pyrrole-2,3,4,5-tetracarboxylates by reaction of dimethyl acetylenedicarboxylate with an amine. Tetrahedron Letters 54:49, pages 6737-6739.
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Mohammad Reza Shushizadeh, Azar Mostoufi, Rashid Badri & Somaye Azizyan. (2013) Marine Sponge/H3PO4: As a Naturally Occurring Chiral Catalyst for Solvent-free Fischer-Indole Synthesis. Jundishapur Journal of Natural Pharmaceutical Products 8:4, pages 160-164.
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Nicholas Douglas, Charles J. Neef, Robert A. Rogers, Jake A. Stanley, Jacob Armitage, Ben Martin, Todd W. Hudnall & William J. Brittain. (2013) Reactivity of tetrahydrochromeno[2,3-b]indoles: chromic indicators of cyanide. Journal of Physical Organic Chemistry 26:8, pages 688-695.
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Long Ren, Zhuangzhi Shi & Ning Jiao. (2013) Pd(II)-catalyzed aerobic oxidative intramolecular hydroamination and C–H functionalization of N-alkynyl anilines for the synthesis of indole derivatives. Tetrahedron 69:22, pages 4408-4414.
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Likai Xia & Yong Rok Lee. (2013) A novel and efficient synthesis of diverse dihydronaphtho[1,2-b]furans using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones to olefins and its application to furomollugin. Organic & Biomolecular Chemistry 11:36, pages 6097.
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Naeem Gulzar & Martin Klussmann. (2013) Aerobic C–H amination of tetrahydrocarbazole derivatives via photochemically generated hydroperoxides. Organic & Biomolecular Chemistry 11:27, pages 4516.
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Bai Lin Li, Dan-Qian Xu & Ai Guo Zhong. (2012) Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fischer indole synthesis in water under microwave irradiation. Journal of Fluorine Chemistry 144, pages 45-50.
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Steffen Müller, Matthew J. Webber & Benjamin List. (2011) The Catalytic Asymmetric Fischer Indolization. Journal of the American Chemical Society 133:46, pages 18534-18537.
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Sambasivarao Kotha, Shilpi Misra & Shaikh M. Mobin. (2010) A new approach to 3-substituted tetrahydro-β-carboline derivative via diethyl acetamidomalonate. Amino Acids 41:4, pages 933-936.
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. 2011. Name Reactions in Heterocyclic Chemistry II. Name Reactions in Heterocyclic Chemistry II 83 212 .
Matthieu Desroses, Krzysztof Wieckowski, Marc Stevens & Luke R. Odell. (2011) A microwave-assisted, propylphosphonic anhydride (T3P®) mediated one-pot Fischer indole synthesis. Tetrahedron Letters 52:34, pages 4417-4420.
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Matyas Tursky, Linda L. R. Lorentz-Petersen, Lasse B. Olsen & Robert Madsen. (2010) Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols. Organic & Biomolecular Chemistry 8:24, pages 5576.
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Kazuhiro Kobayashi, Daisuke Iitsuka, Shuhei Fukamachi & Hisatoshi Konishi. (2009) A convenient synthesis of 2-substituted indoles by the reaction of 2-(chloromethyl)phenyl isocyanides with organolithiums. Tetrahedron 65:36, pages 7523-7526.
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P. Prabhakara Varma, Bailure S. Sherigara, Kittapa M. Mahadevan & Vijaykumar Hulikal. (2009) ChemInform Abstract: Efficient and Straightforward Synthesis of Tetrahydrocarbazoles and 2,3‐Dimethyl Indoles Catalyzed by CAN.. ChemInform 40:24.
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