Literature DB >> 21970468

Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

Yuesi Fang1, Chunrui Wu, Richard C Larock, Feng Shi.   

Abstract

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.

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Year:  2011        PMID: 21970468      PMCID: PMC3209955          DOI: 10.1021/jo201605v

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  44 in total

1.  Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls.

Authors:  Zhijian Liu; Xiaoxia Zhang; Richard C Larock
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

2.  Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Authors:  Chunrui Wu; Yuesi Fang; Richard C Larock; Feng Shi
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

3.  Influence of the aliphatic spacer length on the 5-HT1A receptor activity of new arylpiperazines with an indazole system.

Authors:  M H Paluchowska; B Duszyńska; A Kłodzińska; E Tatarczyńska
Journal:  Pol J Pharmacol       Date:  2000 May-Jun

4.  The direct acyl-alkylation of arynes.

Authors:  Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

5.  Selective palladium-catalyzed cocyclotrimerization of arynes with dimethyl acetylenedicarboxylate: A versatile method for the synthesis of polycyclic aromatic hydrocarbons

Authors: 
Journal:  J Org Chem       Date:  2000-10-20       Impact factor: 4.354

6.  Preparation of polyfunctional indazoles and heteroarylazo compounds using highly functionalized zinc reagents.

Authors:  Benjamin Haag; Zhihua Peng; Paul Knochel
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

7.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

8.  Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation.

Authors:  N Satheesha Rai; Balakrishna Kalluraya; B Lingappa; Shaliny Shenoy; Vedavati G Puranic
Journal:  Eur J Med Chem       Date:  2007-08-30       Impact factor: 6.514

9.  Oxadiazolylindazole sodium channel modulators are neuroprotective toward hippocampal neurones.

Authors:  Lisa A Clutterbuck; Cristina Garcia Posada; Cristina Visintin; Dieter R Riddall; Barrie Lancaster; Paul J Gane; John Garthwaite; David L Selwood
Journal:  J Med Chem       Date:  2009-05-14       Impact factor: 7.446

10.  Alkyne [3 + 2] cycloadditions of iodosydnones toward functionalized 1,3,5-trisubstituted pyrazoles.

Authors:  Duncan L Browne; John B Taylor; Andrew Plant; Joseph P A Harrity
Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354

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  10 in total

1.  Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

Authors:  Expédite Yen-Pon; Pier Alexandre Champagne; Lucie Plougastel; Sandra Gabillet; Pierre Thuéry; Mizuki Johnson; Gilles Muller; Grégory Pieters; Frédéric Taran; K N Houk; Davide Audisio
Journal:  J Am Chem Soc       Date:  2019-01-15       Impact factor: 15.419

2.  Synthesis of [18 F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.

Authors:  Maruthi Kumar Narayanam; Gaoyuan Ma; Pier Alexandre Champagne; Kendall N Houk; Jennifer M Murphy
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-07       Impact factor: 15.336

3.  Influence of Endo- and Exocyclic Heteroatoms on Stabilities and 1,3-Dipolar Cycloaddition Reactivities of Mesoionic Azomethine Ylides and Imines.

Authors:  Pier Alexandre Champagne; K N Houk
Journal:  J Org Chem       Date:  2017-10-06       Impact factor: 4.354

4.  Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Authors:  Travis C McMahon; Jose M Medina; Yun-Fang Yang; Bryan J Simmons; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2015-03-20       Impact factor: 15.419

5.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

6.  Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones.

Authors:  Yuesi Fang; Richard C Larock
Journal:  Tetrahedron       Date:  2012-02-09       Impact factor: 2.457

7.  Synthesis of 2-Alkenyl-2H-indazoles from 2-(2-Carbonylmethyl)-2H-indazoles.

Authors:  Mei-Huey Lin; Kung-Yu Liang; Chang-Hsien Tsai; Yu-Chun Chen; Hung-Chang Hsiao; Yi-Syuan Li; Chung-Hao Chen; Hau-Chun Wu
Journal:  Molecules       Date:  2016-02-19       Impact factor: 4.411

8.  Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents.

Authors:  Jaime Pérez-Villanueva; Lilián Yépez-Mulia; Ignacio González-Sánchez; Juan Francisco Palacios-Espinosa; Olivia Soria-Arteche; Teresita Del Rosario Sainz-Espuñes; Marco A Cerbón; Karen Rodríguez-Villar; Ana Karina Rodríguez-Vicente; Miguel Cortés-Gines; Zeltzin Custodio-Galván; Dante B Estrada-Castro
Journal:  Molecules       Date:  2017-10-31       Impact factor: 4.411

9.  1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.

Authors:  Takashi Ikawa; Shigeaki Masuda; Akira Takagi; Shuji Akai
Journal:  Chem Sci       Date:  2016-04-18       Impact factor: 9.825

Review 10.  [3 + 2]-Cycloaddition reaction of sydnones with alkynes.

Authors:  Veronika Hladíková; Jiří Váňa; Jiří Hanusek
Journal:  Beilstein J Org Chem       Date:  2018-06-05       Impact factor: 2.883

  10 in total

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