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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 12
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Original Articles

A Convenient Synthesis of 4-Chloro- and 4-Bromocinnolines from o-Aminophenylacetylenes

S. F. Vasilevsky Institute of Chemical Kinetics and Combustion Russian Academy of Sciences, 630090, Novosibirsk, Russia
,
E. V. Tretyakov Institute of Chemical Kinetics and Combustion Russian Academy of Sciences, 630090, Novosibirsk, Russia
&
H. D. Verkruijsse Department of Preparative, Organic Chemistry of the University, Padualaan 8, 3584 CH, Utrecht, Netherlands
Pages 1733-1736 | Received 17 Nov 1993, Published online: 23 Sep 2006

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Prasanta Gogoi, Sandhya Rani Gogoi, Namita Devi & Pranjit Barman. (2014) Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones. Synthetic Communications 44:8, pages 1142-1148.
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NataliyaA. Zolnikova, LidiyaG. Fedenok & NikolayE. Polyakov. (2006) IMPROVED METHOD FOR THE CYCLIZATION OF ortho-ALKYNYLBENZENEDIAZONIUM SALTS. Organic Preparations and Procedures International 38:5, pages 476-480.
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Articles from other publishers (27)

A. A. Babushkina, V. N. Mikhailov, A. D. Ogurtsova, A. S. Bunev, V. N. Sorokoumov & I. A. Balova. (2023) The Richter reaction in the synthesis of combretastatin analogs. Russian Chemical Bulletin 72:4, pages 1012-1022.
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Adam Campbell, Paul W. Peterson & Igor V. Alabugin. 2021. Aromaticity. Aromaticity 339 375 .
Fa‐Guang Zhang, Zhen Chen, Chi Wai Cheung & Jun‐An Ma. (2020) Aryl Diazonium Salt‐Triggered Cyclization and Cycloaddition Reactions: Past, Present, and Future . Chinese Journal of Chemistry 38:10, pages 1132-1152.
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Chao Song, Chen Yang, Feifei Zhang, Jinhu Wang & Jin Zhu. (2016) Access to the Cinnoline Scaffold via Rhodium-Catalyzed Intermolecular Cyclization under Mild Conditions. Organic Letters 18:18, pages 4510-4513.
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Satheeshkumar Reddy KandimallaGowravaram Sabitha. (2016) Metal-free C–N bond formations: one-pot synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines, benzo[4′,5']thiazolo- and thiazolo[2′,3′:2,3]imidazo[4,5-c]cinnolines. RSC Advances 6:71, pages 67086-67095.
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Guan-Hua Ma, Xing-Jun Tu, Yi Ning, Bo Jiang & Shu-Jiang Tu. (2014) Efficient Domino Strategy for the Synthesis of Polyfunctionalized Benzofuran-4(5 H )-ones and Cinnoline-4-carboxamides . ACS Combinatorial Science 16:6, pages 281-286.
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Rana K. Mohamed, Paul W. Peterson & Igor V. Alabugin. (2013) Concerted Reactions That Produce Diradicals and Zwitterions: Electronic, Steric, Conformational, and Kinetic Control of Cycloaromatization Processes. Chemical Reviews 113:9, pages 7089-7129.
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Paul W. Peterson, Rana K. Mohamed & Igor V. Alabugin. (2013) How to Lose a Bond in Two Ways ― The Diradical/Zwitterion Dichotomy in Cycloaromatization Reactions. European Journal of Organic Chemistry 2013:13, pages 2505-2527.
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Jabbar Khalafy, Mehdi Rimaz, Mahnaz Ezzati & Rolf H. Prager. (2012) A Green One-Pot Protocol for Regioselective Synthesis of New Substituted 7,8-Dihydrocinnoline-5(6H)-ones. Bulletin of the Korean Chemical Society 33:9, pages 2890-2896.
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N. A. Danilkina, A. E. Kulyashova & I. A. Balova. (2012) Intramolecular cyclizations of functionalized diynes. Chemistry of Heterocyclic Compounds 48:1, pages 95-106.
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A. A. Stepanov, L. M. Gornostaev, S. F. Vasilevsky, E. V. Arnold, V. I. Mamatyuk, D. S. Fadeev, B. Gold & I. V. Alabugin. (2011) Chameleonic Reactivity of Vicinal Diazonium Salt of Acetylenyl-9,10-anthraquinones: Synthetic Application toward Two Heterocyclic Targets. The Journal of Organic Chemistry 76:21, pages 8737-8748.
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Chuan Zhu & Motoki Yamane. (2011) Synthesis of 3,4-disubstituted cinnolines by the Pd-catalyzed annulation of 2-iodophenyltriazenes with an internal alkyne. Tetrahedron 67:26, pages 4933-4938.
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Annelies Goeminne, Peter J. Scammells, Shane M. Devine & Bernard L. Flynn. (2010) Richter cyclization and co-cyclization reactions of triazene-masked diazonium ions. Tetrahedron Letters 51:52, pages 6882-6885.
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Chunhao Yang, Dongdong Chen, Yuyuan Xie & Jian Ding. (2009) Novel Process to 4,4-Dialkyl-1,4-dihydro-6-methoxy-3-phenylcinnolines via Grignard Reaction. HETEROCYCLES 77:1, pages 273.
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Mohamed Hilmy Elnagdi, Nouria A. Al-Awadi & Ismail Abdelshafy Abdelhamid. 2009. 1 43 .
O. V. Vinogradova & I. A. Balova. (2008) Methods for the synthesis of cinnolines (review). Chemistry of Heterocyclic Compounds 44:5, pages 501-522.
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Olga V. Vinogradova, Victor N. Sorokoumov, Sergey F. Vasilevsky & Irina A. Balova. (2007) The Richter reaction of ortho-(alka-1,3-diynyl)aryldiazonium salts. Tetrahedron Letters 48:28, pages 4907-4909.
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Yoshiyuki Hari, Tomoki Kanie & Toyohiko Aoyama. (2006) Efficient synthesis of o-alkynyl-N-pivaloylanilines from o-acyl-N-pivaloylanilines and lithium trimethylsilyldiazomethane. Tetrahedron Letters 47:7, pages 1137-1139.
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Sergei F Vasilevsky, Eugene V Tretyakov & José Elguero. 2002. 1 99 .
E. V. Tretyakov & S. F. Vasilevsky. (1998) Cross-coupling of 4-chloro- and 4-bromocinnolines with alk-1-ynes. Russian Chemical Bulletin 47:6, pages 1233-1234.
Crossref
Eugene V. Tretyakov & Sergei F. Vasilevsky. (1998) NEW FINDINGS IN THE RICHTER REACTION IN SERIES OF VICINAL ALKYNYLPYRAZOLYLDIAZONIUM SALTS. Heterocyclic Communications 4:6.
Crossref
G. Pattenden, J. I. G. Cadogan & S. V. LeyG. Pattenden, J. I. G. Cadogan & S. V. Ley. 1997. Dictionary of Organic Compounds. Dictionary of Organic Compounds 64 84 .
E. V. Tret'yakov & S. F. Vasitevsky. (1996) Synthesis of vicinal aminoiodo- and (acetylamino)iodo-l-alkylpyrazoles. Russian Chemical Bulletin 45:11, pages 2585-2587.
Crossref
Eugene V. Tretyakov & Sergei F. Vasilevsky. (1996) A route to pyrazolylazopyrazolo[4,3-c]pyrazoles via l,5-dimethyl-3R-pyrazolyl-4-diazonium salts. Mendeleev Communications 6:5, pages 190-191.
Crossref
Sergei F. Vasilevsky & Eugene V. Tretyakov. (2006) Cinnolines and pyrazolopyridazines. — Novel synthetic and mechanistic aspects of the Richter reaction. Liebigs Annalen 1995:5, pages 775-779.
Crossref
G. Heinisch & B. Matuszczak. 1995. 226 243 .
S. F. VASILEVSKY, E. V. TRETYAKOV & H. D. VERKRUIJSSE. (2010) ChemInform Abstract: A Convenient Synthesis of 4‐Chloro‐ and 4‐Bromocinnolines (II) from o‐ Aminophenylacetylenes (I).. ChemInform 25:50.
Crossref

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