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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 20
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Original Articles

2,3-Pyridyne Formation by Fluoride-Induced Desilylation-Elimination

Michael A. Walters 6128 Burke Laboratory, Department of Chemistry, Dartmouth College, Hanover, NH, 03755
&
John J. Shay 6128 Burke Laboratory, Department of Chemistry, Dartmouth College, Hanover, NH, 03755
Pages 3573-3579 | Received 28 Apr 1997, Published online: 22 Aug 2006

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Emily Carlson, Guillaume Duret, Nicolas Blanchard & William Tam. (2016) Synthesis of cyclopropanated [2.2.1] heterobicycloalkenes: An improved procedure. Synthetic Communications 46:1, pages 55-62.
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Articles from other publishers (37)

Sarah N. Hancock, Nattawut Yuntawattana, Sara M. Valdez & Quentin Michaudel. (2022) Expedient synthesis and ring-opening metathesis polymerization of pyridinonorbornenes. Polymer Chemistry 13:39, pages 5530-5535.
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Avishek Guin, Subrata Bhattacharjee & Akkattu T. Biju. 2021. DNA‐ and RNA‐Based Computing Systems. DNA‐ and RNA‐Based Computing Systems 359 406 .
Jiarong Shi, Lianggui Li & Yang Li. (2021) o -Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors . Chemical Reviews 121:7, pages 3892-4044.
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Takamitsu Hosoya, Suguru Yoshida & Yu Nakamura. (2019) Recent Advances in Synthetic Hetaryne Chemistry. HETEROCYCLES 98:12, pages 1623.
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Naoko Takenaga, Shohei Ueda, Takumi Hayashi, Toshifumi Dohi & Shinji Kitagaki. (2019) Vicinal Functionalization of Uracil Heterocycles with Base Activation of Iodonium(III) Salts. HETEROCYCLES 99:2, pages 865.
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Saber Mirzaei & Hormoz Khosravi. (2017) Predicting the regioselectivity of nucleophilic addition to arynes using frontier molecular orbital contribution analysis. Tetrahedron Letters 58:34, pages 3362-3365.
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Debapratim Das, Puja Poddar, Saurabh Maity & Rajarshi Samanta. (2017) Rhodium(III)-Catalyzed C6-Selective Arylation of 2-Pyridones and Related Heterocycles Using Quinone Diazides: Syntheses of Heteroarylated Phenols. The Journal of Organic Chemistry 82:7, pages 3612-3621.
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Jose M. Medina, Moritz K. Jackl, Robert B. Susick & Neil K. Garg. (2016) Synthetic studies pertaining to the 2,3-pyridyne and 4,5-pyrimidyne. Tetrahedron 72:26, pages 3629-3634.
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Jong-Liang Lin, Chia-Hao Ye, Bo-Chiuan Lin, Szu-Hui Li, Zi-Xian Yang, Yu-Hsien Chiang, Shang-Wei Chen, Chia-Hsin Wang, Yaw-Wen Yang & Jiing-Chyuan Lin. (2015) Thermal Reaction of 2,4-Dibromopyridine on Cu(100). The Journal of Physical Chemistry C 119:47, pages 26471-26480.
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Adam E. Goetz, Tejas K. Shah & Neil K. Garg. (2015) Pyridynes and indolynes as building blocks for functionalized heterocycles and natural products. Chemical Communications 51:1, pages 34-45.
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Yoshihiro Sato, Nozomi Saito & Ken-ichi Nakamura. (2014) 1,3-Dipolar Cycloaddition of Pyridynes and Azides: Concise Synthesis of Triazolopyridines. HETEROCYCLES 88:2, pages 929.
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Nozomi Saito, Ken-ichi Nakamura, Sayako Shibano, Soichiro Ide, Masabumi Minami & Yoshihiro Sato. (2013) Addition of Cyclic Ureas and 1-Methyl-2-oxazolidone to Pyridynes: A New Approach to Pyridodiazepines, Pyridodiazocines, and Pyridooxazepines. Organic Letters 15:2, pages 386-389.
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Adam E. Goetz & Neil K. Garg. (2012) Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model. Nature Chemistry 5:1, pages 54-60.
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Yuesi Fang & Richard C. Larock. (2012) Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones. Tetrahedron 68:13, pages 2819-2826.
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Adam E. Goetz, Sarah M. Bronner, Jordan D. Cisneros, Joshua M. Melamed, Robert S. Paton, K. N. Houk & Neil K. Garg. (2012) An Efficient Computational Model to Predict the Synthetic Utility of Heterocyclic Arynes. Angewandte Chemie International Edition 51:11, pages 2758-2762.
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Adam E. Goetz, Sarah M. Bronner, Jordan D. Cisneros, Joshua M. Melamed, Robert S. Paton, K. N. Houk & Neil K. Garg. (2012) An Efficient Computational Model to Predict the Synthetic Utility of Heterocyclic Arynes. Angewandte Chemie 124:11, pages 2812-2816.
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Lingyong Jiang, Xingxin Yu, Bing Fang & Jie Wu. (2012) Silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with pyridyne. Organic & Biomolecular Chemistry 10:40, pages 8102.
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Yuesi Fang, Chunrui Wu, Richard C. Larock & Feng Shi. (2011) Synthesis of 2 H -Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes . The Journal of Organic Chemistry 76:21, pages 8840-8851.
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Nathan J. Rau & Paul G. Wenthold. (2011) Experimental Investigation of the Absolute Enthalpies of Formation of 2,3-, 2,4-, and 3,4-Pyridynes. The Journal of Physical Chemistry A 115:37, pages 10353-10362.
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Trung D. Nguyen, Robert Webster & Mark Lautens. (2011) Rh(I)-Catalyzed Ring-Opening of Hetaryne−Furan Diels−Alder Adducts: Rapid Access to Stereochemically Defined Heterocyclic Scaffolds. Organic Letters 13:6, pages 1370-1373.
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Monica F. Enamorado, Pauline W. Ondachi & Daniel L. Comins. (2010) A Five-Step Synthesis of ( S )-Macrostomine from ( S )-Nicotine . Organic Letters 12:20, pages 4513-4515.
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Mihai S. Viciu, Lekha Gupta & David B. Collum. (2010) Mechanism of Lithium Diisopropylamide-Mediated Substitution of 2,6-Difluoropyridine. Journal of the American Chemical Society 132:18, pages 6361-6365.
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Gregory L. Beutner, Jeffrey T. Kuethe, Mary M. Kim & Nobuyoshi Yasuda. (2008) Expedient Synthesis of 3-Alkoxymethyl- and 3-Aminomethyl-Pyrazolo[3,4- b ]pyridines . The Journal of Organic Chemistry 74:2, pages 789-794.
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F. Ivy Carroll. (2009) Epibatidine Analogs Synthesized for Characterization of Nicotinic Pharmacophores—A Review. HETEROCYCLES 79:1, pages 99.
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Toshihiko Iwayama & Yoshihiro Sato. (2009) Nickel(0)-catalyzed [2 + 2 + 2] cycloaddition of diynes and 3,4-pyridynes: novel synthesis of isoquinoline derivatives. Chemical Communications:35, pages 5245.
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F. Ivy Carroll, T. Philip Robinson, Lawrence E. Brieaddy, Robert N. Atkinson, S. Wayne Mascarella, M. Imad Damaj, Billy R. Martin & Hernán A. Navarro. (2007) Synthesis and Nicotinic Acetylcholine Receptor Binding Properties of Bridged and Fused Ring Analogues of Epibatidine. Journal of Medicinal Chemistry 50:25, pages 6383-6391.
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Hai-Chuan Liu, Xin-Hao Zhang, Changsheng Wang, Yun-Dong Wu & Shihe Yang. (2007) Pyridyne radical cations produced by photodissociation of Mg ˙+ (multifluoro-pyridine) complexes: A combined experimental and theoretical study . Phys. Chem. Chem. Phys. 9:5, pages 607-615.
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Hiroto Yoshida, Junnai Ikadai, Miwa Shudo, Joji Ohshita & Atsutaka Kunai. (2004) Addition of Silicon−Silicon σ-Bonds to Arynes or Bisarynes Catalyzed by a Palladium Complex. Organometallics 24:1, pages 156-162.
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Stephen J. Connon & Anthony F. Hegarty. (2004) Stabilised 2,3‐Pyridyne Reactive Intermediates of Exceptional Dienophilicity. European Journal of Organic Chemistry 2004:16, pages 3477-3483.
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Natacha Mariet, Malika Ibrahim-Ouali, Jean-Luc Parrain & Maurice Santelli. (2004) Structure of pyridynes and pyridyne N-oxides and their cycloaddition to ketene dialkyl acetals. Journal of Molecular Structure: THEOCHEM 679:1-2, pages 53-58.
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Rafael Chinchilla, Carmen Nájera & Miguel Yus. (2004) Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry. Chemical Reviews 104:5, pages 2667-2722.
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Ronald N. Warrener. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Basudeb Basu, Satadru Jha, Niranjan K. Mridha & Md.Mosharef H. Bhuiyan. (2002) Palladium-catalysed amination of halopyridines on a KF-alumina surface. Tetrahedron Letters 43:44, pages 7967-7969.
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Joseph R. Lennox, Sean C. Turner & Henry Rapoport. (2001) Enantiospecific Synthesis of Annulated Nicotine Analogues from d -Glutamic Acid. 7-Azabicyclo[2.2.1]heptano[2.3- c ]pyridines . The Journal of Organic Chemistry 66:21, pages 7078-7083.
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M. A. WALTERS & J. J. SHAY. (2010) ChemInform Abstract: 2,3‐Pyridyne Formation by Fluoride‐Induced Desilylation‐Elimination.. ChemInform 29:1.
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Colin P. Dell. (1998) Cycloadditions in synthesis. Journal of the Chemical Society, Perkin Transactions 1:22, pages 3873.
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Robert D. Larsen. 1998. A critical review of the 1997 literature preceded by two chapters on current heterocyclic topics. A critical review of the 1997 literature preceded by two chapters on current heterocyclic topics 226 250 .

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