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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 22
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Original Articles

Imino Diels–Alder Reactions: Efficient Synthesis of Pyrano and Furoquinolines Catalyzed by ZrCl4

M. Mahesh Organic Chemistry Division‐II, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
Ch. Venkateshwar Reddy Organic Chemistry Division‐II, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
K. Srinivasa Reddy Organic Chemistry Division‐II, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
P. V. K. Raju Organic Chemistry Division‐II, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
&
V. V. Narayana Reddy Organic Chemistry Division‐II, Indian Institute of Chemical Technology, Hyderabad, 500 007, IndiaCorrespondence[email protected]
Pages 4089-4104 | Received 13 Jul 2004, Published online: 10 Jan 2011

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Ravinder Goud Puligoundla, Hanmanth Reddy Vulupala, Nagaiah Kommu & Sudhakar Babu Kondra. (2015) Ceric Ammonium Nitrate (CAN)–Catalyzed, Efficient, One-Pot, Three-Component, aza-Diels–Alder Reactions for a Facile Synthesis of Tetrahydropyranoquinoline Derivatives. Synthetic Communications 45:4, pages 494-502.
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Articles from other publishers (37)

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Palani Amudha, Gnanamani Lavanya, Karuppan Venkatapathy & Chinnian Jayaraman Magesh. (2019) Choline Chloride: Zinc Chloride Ionic Liquid Mediated Inverse Electron Demand (IED) Diels-Alder Reaction; An eco-benign Synthesis of Pyranoquinolines and Furanoquinolines. Letters in Organic Chemistry 16:11, pages 865-873.
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Noriyoshi Arai & Takeshi Ohkuma. (2017) Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation. The Journal of Organic Chemistry 82:14, pages 7628-7636.
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Malose J. Mphahlele. (2016) 2,6,8-Triaryl-3-iodoquinolin-4(1 H )-ones as Substrates for the Synthesis of 2,3,6,8-Tetraarylquinolin-4(1 H )-ones and the 2-Substituted 4,6,8-Triaryl-1 H -furo[3,2- c ]quinolines . Journal of Heterocyclic Chemistry 53:5, pages 1378-1385.
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Kobra Nikoofar & Zahra Khademi. (2015) A review on green Lewis acids: zirconium(IV) oxydichloride octahydrate (ZrOCl2·8H2O) and zirconium(IV) tetrachloride (ZrCl4) in organic chemistry. Research on Chemical Intermediates 42:5, pages 3929-3977.
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Mehdi Rimaz, Zahra Jalalian, Hossein Mousavi & Rolf H. Prager. (2016) Base organocatalyst mediated annulation of arylglyoxalmonohydrates with 2,4-dihydroxyquinoline to form new pyranodiquinolinones. Tetrahedron Letters 57:1, pages 105-109.
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Mohammad Reza Shushizadeh, Azar Mostoufi, Abdol-azim Behfar & Minoo Heidary. (2015) 1,7-Sigmatropic rearrangement in 1,2-dihydro and 1,2,3,4-tetrahydroquinoline synthesis using marine sponge/H2C2O4 as a catalyst. Arabian Journal of Chemistry 8:6, pages 868-872.
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E. Rajanarendar, M. Nagi Reddy, K. Govardhan Reddy & S. Rama Krishna. (2012) l-Proline catalyzed efficient one-pot three-component aza-Diels–Alder reactions on nitrostyrylisoxazoles: a facile synthesis of new isoxazolyl tetrahydroquinolines and isoxazolo[2,3-a]pyrimidines. Tetrahedron Letters 53:23, pages 2909-2913.
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Ghazwan Ali Salman, Riffat Un Nisa, Viktor O. Iaroshenko, Jamshed Iqbal, Khurshid Ayub & Peter Langer. (2012) Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study. Organic & Biomolecular Chemistry 10:47, pages 9464.
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Nitu Mahajan, Surrinder Koul & Tej K. Razdan. (2011) Bismuth triflate–L(−)‐proline catalyzed synthesis of chiral 2,5‐diaryl‐2,3‐dihydropyrano[2,3‐b]quinolin‐4‐ones. Journal of Heterocyclic Chemistry 48:6, pages 1302-1307.
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. 2011. Name Reactions in Heterocyclic Chemistry II. Name Reactions in Heterocyclic Chemistry II 351 399 .
Ye Chen & Yong-Rok Lee. (2011) FeCl 3 -Catalyzed Synthesis of 2-Methyl-4-Substituted-1,2,3,4-Tetrahydroquinoline Derivatives by the Imino Diels-Alder Reaction . Bulletin of the Korean Chemical Society 32:7, pages 2485-2488.
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Lingaiah Nagarapu, Rajashaker Bantu & Ravinder Goud Puligoundla. (2011) Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives. European Journal of Chemistry 2:2, pages 260-265.
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Wim Van Snick, Anastasia Parchina & Wim Dehaen. (2011) Efficient three-component synthesis of tetrahydrothieno[3,2-f]quinolines. Tetrahedron 67:23, pages 4179-4184.
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Atul Kumar, Suman Srivastava, Garima Gupta, Vinita Chaturvedi, Sudhir Sinha & R. Srivastava. (2010) Natural Product Inspired Diversity Oriented Synthesis of Tetrahydroquinoline Scaffolds as Antitubercular Agent. ACS Combinatorial Science 13:1, pages 65-71.
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Emese Gál, Castelia Cristea, Luminita Silaghi-Dumitrescu, Tamás Lovász & Antal Csámpai. (2010) Iodine-catalyzed stepwise [4+2] cycloaddition of phenothiazine- and ferrocene-containing Schiff bases with DHP promoted by microwave irradiation. Tetrahedron 66:52, pages 9938-9944.
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C. S. KavithaK. M. HosamaniR. S. Harisha. (2010) Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride. Canadian Journal of Chemistry 88:5, pages 443-452.
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Vinod T. Kamble, Bhaskar S. Davane, Sanjay A. Chavan, Dnyanoba B. Muley & Sandeep T. Atkore. (2010) Imino Diels–Alder reactions: One-pot synthesis of tetrahydroquinolines. Chinese Chemical Letters 21:3, pages 265-268.
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Kai Schiemann, Dirk Finsinger, Frank Zenke, Christiane Amendt, Thorsten Knöchel, David Bruge, Hans-Peter Buchstaller, Ulrich Emde, Wolfgang Stähle & Soheila Anzali. (2010) The discovery and optimization of hexahydro-2H-pyrano[3,2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5. Bioorganic & Medicinal Chemistry Letters 20:5, pages 1491-1495.
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Ritwik Burai, Chinnasamy Ramesh, Marvin Shorty, Ramona Curpan, Cristian Bologa, Larry A. Sklar, Tudor Oprea, Eric R. Prossnitz & Jeffrey B. Arterburn. (2010) Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs. Organic & Biomolecular Chemistry 8:9, pages 2252.
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Jianjun Li, Jia Li & Weike Su. (2009) Proline triflate catalysed Diels–Alder reaction in the synthesis of tetrahydroquinoline derivatives. Journal of Chemical Research 2009:8, pages 499-504.
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Xiang-Shan Wang, Qing Li, Jian-Rong Wu & Shu-Jiang Tu. (2009) Efficient Method for the Synthesis of Pyranoquinoline, Thiopyranoquinoline, Thienoquinoline, and Naphtho[2,7]naphthyridine Derivatives Catalyzed by Iodine. Journal of Combinatorial Chemistry 11:3, pages 433-437.
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Vladimir V. Kouznetsov. (2009) Recent synthetic developments in a powerful imino Diels–Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids. Tetrahedron 65:14, pages 2721-2750.
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Aswathanarayana Srinivasa, Kittappa M. Mahadevan & Vijaykumar Hulikal. (2008) Imino Diels-Alder Reactions: Efficient Synthesis of 2-Aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by Antimony(III) Sulfate. Monatshefte für Chemie - Chemical Monthly 139:3, pages 255-259.
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Kentaro Asahi & Hiroshi Nishino. (2008) Manganese(III)-based dioxapropellane synthesis using tricarbonyl compounds. Tetrahedron 64:8, pages 1620-1634.
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Aswathanarayana Srinivasa, Kittappa Malavalli Mahadevan, Kallappa Mahadevappa Hosamani & Vijaykumar Hulikal. (2008) Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid. Monatshefte für Chemie - Chemical Monthly 139:2, pages 141-145.
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A.J. Phillips, J.A. Henderson & K.L. Jackson. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 337 418 .
Zhuqing Zhou, Fan Xu, Xiaoyan Han, Jun Zhou & Qi Shen. (2007) Stereoselective Synthesis of Pyrano[3,2-c]- and Furano[3,2-c]quinolines: Samarium Diiodide-Catalyzed One-Pot Aza-Diels–Alder Reactions. European Journal of Organic Chemistry 2007:31, pages 5265-5269.
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Mrityunjay K. Singh, Atish Chandra, Bhawana Singh & Radhey M. Singh. (2007) Synthesis of diastereomeric 2,4-disubstituted pyrano[2,3-b]quinolines from 3-formyl-2-quinolones through O–C bond formation via intramolecular electrophilic cyclization. Tetrahedron Letters 48:34, pages 5987-5990.
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K Srinivasa Reddy, Ch. Venkateshwar Reddy, M Mahesh, K Rosi Reddy, P VK Raju & V V Narayana Reddy. (2007) Zirconium(IV) chloride-catalyzed synthesis of 1,5-benzodiazepine derivatives. Canadian Journal of Chemistry 85:3, pages 184-188.
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Deepali Mahajan, Bilal A. Ganai, Rattan Lal Sharma & Kamal K. Kapoor. (2006) Antimony chloride doped on hydroxyapetite catalyzed stereoselective one-pot synthesis of pyrano[3,2-c]quinolines. Tetrahedron Letters 47:45, pages 7919-7921.
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Kentaro Asahi & Hiroshi Nishino. (2006) Synthesis of heterocyclic propellanes using Mn(III)-based oxidative cyclization. Tetrahedron Letters 47:40, pages 7259-7262.
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Gourhari Maiti & Pradip Kundu. (2006) Imino Diels–Alder reactions: an efficient one-pot synthesis of pyrano and furanoquinoline derivatives catalyzed by SbCl3. Tetrahedron Letters 47:32, pages 5733-5736.
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Kentaro Asahi & Hiroshi Nishino. (2005) Manganese(III)-based oxidation of 2,4-piperidinediones in the presence of alkenes. Tetrahedron 61:47, pages 11107-11124.
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M. Mahesh, Ch. Venkateshwar Reddy, K. Srinivasa Reddy, P. V. K. Raju & V. V. Narayana Reddy. (2005) Imino Diels—Alder Reactions: Efficient Synthesis of Pyrano and Furoquinolines Catalyzed by ZrCl 4 . . ChemInform 36:16.
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