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Collect. Czech. Chem. Commun. 2009, 74, 957-972
https://doi.org/10.1135/cccc2009014
Published online 2009-06-18 10:32:42

Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides

Tienan Jin*, Fan Yang and Yoshinori Yamamoto*

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

Crossref Cited-by Linking

  • Meerakrishna Ramakrishnan Suseela, Smile Suresh Snoxma, Athira Mohanakumaran, Choutipalli Venkata Surya Kumar, Shanmugam Ponnusamy: Diverse reactivity of isatin-based N,N′-cyclic azomethine imine dipoles with arynes: synthesis of 1′-methyl-2′-oxospiro [indene-1,3′-indolines] and 3-aryl-3-pyrazol-2-oxindoles. New J. Chem. 2020, 44, 11593. <https://doi.org/10.1039/D0NJ01684E>
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  • Liu Zhenxing, Wang Long, Tan Haocheng, Zhou Shiyi, Fu Tianren, Xia Ying, Zhang Yan, Wang Jianbo: Synthesis of 1H-indazoles from N-tosylhydrazones and nitroaromatic compounds. Chem. Commun. 2014, 50, 5061. <https://doi.org/10.1039/C4CC00962B>
  • Chattha Fauzia Anjum, Munawar Munawar Ali, Nagra Saeed Ahmad, Ashraf Mohammad, Khan Misbahul Ain, Kosur Samina: Synthesis of 3-Aryl-1H-Indazoles and Their Effects on Plant Growth. J Plant Growth Regul 2013, 32, 291. <https://doi.org/10.1007/s00344-012-9297-1>
  • Li Pan, Wu Chunrui, Zhao Jingjing, Li Yang, Xue Weichao, Shi Feng: One-pot synthesis of dihydrobenzisoxazoles from hydroxylamines, acetylenedicarboxylates, and arynes via in situ generation of nitrones. Can. J. Chem. 2013, 91, 43. <https://doi.org/10.1139/cjc-2012-0199>
  • Wang Chiou-Dong, Liu Rai-Shung: Silver-catalyzed [3+2]-cycloaddition of benzynes with diazocarbonyl species via a postulated (1H-indazol-1-yl)silver intermediate. Org. Biomol. Chem. 2012, 10, 8948. <https://doi.org/10.1039/c2ob26760h>
  • Xin Yong, Zhao Jingwei, Gu Jiwei, Zhu Shizheng: Catalyst free 1,3-dipolar cycloaddition of 3-oxo-1,2-pyrazolidinium ylides to β-trifluoroacetyl vinyl ethyl ether: Synthesis of 6-trifluoroacetyl substituted bicyclic pyrazolidinones. J FLUORINE CHEM 2011, 132, 402. <https://doi.org/10.1016/j.jfluchem.2011.03.023>
  • Spiteri Christian, Sharma Pallavi, Zhang Fengzhi, Macdonald Simon J. F., Keeling Steve, Moses John E.: An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne. Chem. Commun. 2010, 46, 1272. <https://doi.org/10.1039/b922489k>
  • Jin Tienan, Yang Fan, Yamamoto Yoshinori: ChemInform Abstract: Facile and Efficient Synthesis of Indazole Derivatives by 1,3‐Cycloaddition of Arynes with Diazo Compounds and Azomethine Imides. ChemInform 2009, 40. <https://doi.org/10.1002/chin.200946123>